33483-65-7

Basic information

• Product Name: trans-4-Methylcyclohexylamine hydrochloride
• Synonyms: TRANS-4-METHYL-CYCLOHEXYLAMINE HCL;TRANS-4-METHYLCYCLOHEXYLAMINE HYDROCHLORIDE
• CAS NO: 33483-65-7
• Molecular Formula: C7H16ClN
• Molecular Weight: 149.66
• Mol File: 33483-65-7.mol
• Article Data: 30

Chemical Properties

• Melting Point: 260 °C
• Boiling Point: 195.9 °C at 760 mmHg
• Flash Point: 72.3 °C
• Appearance: /
• Vapor Pressure: 0.347mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: trans-4-Methylcyclohexylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-Methylcyclohexylamine hydrochloride(33483-65-7)
• EPA Substance Registry System: trans-4-Methylcyclohexylamine hydrochloride(33483-65-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 33483-65-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H15N.ClH/c1-6-2-4-7(8)5-3-6;/h6-7H,2-5,8H2,1H3;1H/t6-,7-;

Synthetic route

trans-4-methylcyclohexylamine hydrochloride (100959-19-1) → trans-4-methylcyclohexylamine hydrochloride (33483-65-7)

Conditions	Yield
In methanol; acetone at 25 - 30℃; for 3h;

formic acid (64-18-6) + trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → N-(4-methylcyclohexyl)formamide (26003-39-4)

Conditions	Yield
With sodium formate at 120 - 140℃; for 2h;

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → trans-N,4-dimethylcyclohexylamine (2523-88-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCO2Na / 2 h / 120 - 140 °C 2: LiAlH4 / diethyl ether View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → trans-4.N-Dimetil-N-(2.4-dinitrofenil)cicloesilammina (25886-43-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: HCO2Na / 2 h / 120 - 140 °C 2: LiAlH4 / diethyl ether 3: NaOEt / ethanol / Heating View Scheme

quinoxaline-2-carboxylic acid chloride (54745-92-5) + ethyl acetate n-hexane + trans-4-methylcyclohexylamine hydrochloride (33483-65-7) + 1-methylcyclohexan-4-one (589-92-4) → N-(trans-4-methylcyclohexyl)-2-quinoxalinecarboxamide (226877-90-3) + N-(trans-4-Methylcyclohexyl)-2-qulinoxalinecarboxamide

Conditions	Yield
With pyridine; hydroxylamine In ethanol; dichloromethane; water; ethyl acetate

2-amino-4-chloropyrimidine (3993-78-0) + trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → N4-((1r,4r)-4-methylcyclohexyl)pyridine-2,4-diamine (1401034-42-1)

Conditions	Yield
With triethylamine In butan-1-ol for 36h; Reflux;
With triethylamine In butan-1-ol for 36h; Reflux; Inert atmosphere;	1770 g

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 9-((1r,4r)-4-methylcyclohexyl)-N-(5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine (1401033-82-6)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 View Scheme
Multi-step reaction with 6 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux; Inert atmosphere 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2.16 h / 10 - 20 °C / Inert atmosphere 3.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 2.25 h / -74 - 0 °C / Inert atmosphere 3.2: 0.58 h / -60 °C / Inert atmosphere 3.3: Reflux; Inert atmosphere 4.1: lithium hexamethyldisilazane / 1-methyl-pyrrolidin-2-one / 90 °C / Inert atmosphere 5.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / 1,4-dioxane / 0.17 h / Inert atmosphere 5.2: 3 h / 100 °C / Inert atmosphere 6.1: hydrogenchloride; water / methanol / 20 °C / Inert atmosphere View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 5-iodo-N4-((1R,4R)-4-methylcyclohexyl)pyrimidine-2,4-diamine (1401034-43-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / butan-1-ol / 36 h / Reflux 2: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: triethylamine / butan-1-ol / 36 h / Reflux; Inert atmosphere 2: N-iodo-succinimide / N,N-dimethyl-formamide / 2.16 h / 10 - 20 °C / Inert atmosphere View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 5-(3-fluoropyridin-4-yl)-N4-((1R,4R)-4-methylcyclohexyl)pyrimidine-2,4-diamine (1401034-44-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / butan-1-ol / 36 h / Reflux 2: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux; Inert atmosphere 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2.16 h / 10 - 20 °C / Inert atmosphere 3.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 2.25 h / -74 - 0 °C / Inert atmosphere 3.2: 0.58 h / -60 °C / Inert atmosphere 3.3: Reflux; Inert atmosphere View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine (1401034-45-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / butan-1-ol / 36 h / Reflux 2: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux; Inert atmosphere 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2.16 h / 10 - 20 °C / Inert atmosphere 3.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 2.25 h / -74 - 0 °C / Inert atmosphere 3.2: 0.58 h / -60 °C / Inert atmosphere 3.3: Reflux; Inert atmosphere 4.1: lithium hexamethyldisilazane / 1-methyl-pyrrolidin-2-one / 90 °C / Inert atmosphere View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → tert-butyl 2-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (1401034-46-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: triethylamine / butan-1-ol / 36 h / Reflux 2: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5: sodium t-butanolate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux; Inert atmosphere 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2.16 h / 10 - 20 °C / Inert atmosphere 3.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 2.25 h / -74 - 0 °C / Inert atmosphere 3.2: 0.58 h / -60 °C / Inert atmosphere 3.3: Reflux; Inert atmosphere 4.1: lithium hexamethyldisilazane / 1-methyl-pyrrolidin-2-one / 90 °C / Inert atmosphere 5.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / 1,4-dioxane / 0.17 h / Inert atmosphere 5.2: 3 h / 100 °C / Inert atmosphere View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 1-[2-({9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl}amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]ethanone

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: 1,4-dioxane / 0.17 h View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 2-[2-({9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-y}amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]ethanol (1401033-84-8)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: 1,4-dioxane / 0.08 h 6.2: 0.17 h 7.1: hydrogenchloride / 1,4-dioxane / 0.5 h View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 2-(2-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)-2-oxoethyl acetate (1401034-47-6)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux; Inert atmosphere 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2.16 h / 10 - 20 °C / Inert atmosphere 3.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 2.25 h / -74 - 0 °C / Inert atmosphere 3.2: 0.58 h / -60 °C / Inert atmosphere 3.3: Reflux; Inert atmosphere 4.1: lithium hexamethyldisilazane / 1-methyl-pyrrolidin-2-one / 90 °C / Inert atmosphere 5.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / 1,4-dioxane / 0.17 h / Inert atmosphere 5.2: 3 h / 100 °C / Inert atmosphere 6.1: hydrogenchloride; water / methanol / 20 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C / Inert atmosphere View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 2-hydroxy-1-(2-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)ethanone (1401033-86-0)

Conditions	Yield
Multi-step reaction with 7 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C 7.1: sodium methylate / dichloromethane; methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux; Inert atmosphere 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2.16 h / 10 - 20 °C / Inert atmosphere 3.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 2.25 h / -74 - 0 °C / Inert atmosphere 3.2: 0.58 h / -60 °C / Inert atmosphere 3.3: Reflux; Inert atmosphere 4.1: lithium hexamethyldisilazane / 1-methyl-pyrrolidin-2-one / 90 °C / Inert atmosphere 5.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / 1,4-dioxane / 0.17 h / Inert atmosphere 5.2: 3 h / 100 °C / Inert atmosphere 6.1: hydrogenchloride; water / methanol / 20 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C / Inert atmosphere 8.1: methanol; sodium methylate / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 2-hydroxy-1-(2-((9-((1R,4R)-4-methylcyclohexyl)-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)ethanone hydrochloride (1401034-19-2)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C 7.1: sodium methylate / dichloromethane; methanol / 1 h / 20 °C 8.1: hydrogenchloride / water View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 2-[2-({9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl}amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]-2-oxoacetic acid (1401033-87-1)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: pyridine / tetrahydrofuran / 20 °C 7.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → methyl 2-{[6-(2-methoxy-2-oxoacetyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl]{9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl}amino}-2-oxoacetate (1401034-48-7)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: pyridine / tetrahydrofuran / 20 °C View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 9-[(1r,4r)-4-methylcyclohexyl]-N-[6-(3,3,3-trifluoropropyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine (1401033-88-2)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: sodium tris(acetoxy)borohydride / 1,4-dioxane / 0.25 h View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → N-[6-(2-fluoroethyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl]-9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine (1401033-90-6)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N,N-dimethyl-formamide; ethanol / 8.67 h / 90 °C View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → N-[6-(2-methoxyethyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl]-9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine (1401033-91-7)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 °C View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → tert-butyl 8-methyl-2-({9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl}amino)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (1401034-52-3)

Conditions

Yield

Multi-step reaction with 5 steps 1: triethylamine / butan-1-ol / 36 h / Reflux 2: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 1.5 h / 100 °C / Microwave radiation View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 5-(5-fluoro-2-methoxypyridin-4-yl)-N4-[(1r,4r)-4-methylcyclohexyl]pyrimidine-2,4-diamine (1401034-56-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran / 1.83 h / -78 °C 3.2: Reflux View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → 6-methoxy-9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine (1401034-57-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran / 1.83 h / -78 °C 3.2: Reflux 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 105 °C / Inert atmosphere View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → (S)-2-hydroxy-1-[2-({9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl}amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]propan-1-one (1401034-13-6)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1,2-dichloro-ethane / chloroform / 4 h / 20 °C View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → C26H29N7O2*(x)H3O4P

Conditions

Yield

Multi-step reaction with 8 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C 7.1: sodium methylate / dichloromethane; methanol / 1 h / 20 °C 8.1: phosphoric acid / dichloromethane; ethanol / 0.02 h View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → (x)C6H8O7*C26H29N7O2

Conditions

Yield

Multi-step reaction with 8 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C 7.1: sodium methylate / dichloromethane; methanol / 1 h / 20 °C 8.1: dichloromethane; ethanol / 0.02 h View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → (x)C4H6O6*C26H29N7O2

Conditions

Yield

Multi-step reaction with 8 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C 7.1: sodium methylate / dichloromethane; methanol / 1 h / 20 °C 8.1: dichloromethane; ethanol / 0.02 h View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → (x)C7H6O3*C26H29N7O2

Conditions

Yield

Multi-step reaction with 8 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C 7.1: sodium methylate / dichloromethane; methanol / 1 h / 20 °C 8.1: dichloromethane; ethanol / 0.02 h View Scheme

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → (x)C6H6O3S*C26H29N7O2

Conditions

Yield

Multi-step reaction with 8 steps 1.1: triethylamine / butan-1-ol / 36 h / Reflux 2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 10 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / Reflux 4.1: lithium hexamethyldisilazane / toluene; 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 90 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 20 °C 5.2: 0 °C / pH 9 6.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h / 20 °C 7.1: sodium methylate / dichloromethane; methanol / 1 h / 20 °C 8.1: dichloromethane; ethanol / 0.02 h View Scheme

Upstream product

• 100959-19-1 trans-4-methylcyclohexylamine hydrochloride 
• 393-11-3 4-nitro-3-(trifluoromethyl)benzeneamine 
• 98-08-8 α,α,α-trifluorotoluene 
• 75-61-6 dibromodifluoromethane 
• 88-73-3 2-Chloronitrobenzene 
• 98-95-3 nitrobenzene 
• 76-05-1 trifluoroacetic acid 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 612-24-8 o-nitrobenzonitrile 
• 528-29-0 1,2-Dinitrobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 77152-08-0 trifluoromethylcopper(I) 
• 609-73-4 o-nitroiodobenzene 
• 116965-16-3 3-nitro-4-(trifluoromethyl)benzoic acid 

Downstream Products

• 1588959-89-0 C₂₅H₂₈N₈O 
• 1588959-87-8 1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperidin-4-one 
• 1588959-06-1 8-(2-methoxy-6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)-1,8-diazaspiro[4.5]decan-2-one 
• 1588959-04-9 8-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)-1,8-diazaspiro[4.5]decan-2-one 
• 1588959-02-7 8-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)-2-thia-8-azaspiro[4.5]-decane 2,2-dioxide 
• 1588959-00-5 9-((1r,4r)-4-methylcyclohexyl)-N-(6-(4-((methylsulfonyl)methyl)-piperidin-1-yl)pyridazin-3-yl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1588958-98-8 2-hydroxy-1-(4-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperazin-1-yl)ethanone 
• 1588958-96-6 (R)-1-(methyl(1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido-[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperidin-4-yl)amino)propan-2-ol 
• 1588958-94-4 N-(5-(4-(dimethylamino)piperidin-1-yl)-6-methoxypyridin-2-yl)-9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1588958-92-2 N-(5-(4-(dimethylamino)piperidin-1-yl)-6-fluoropyridin-2-yl)-9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1588958-90-0 N-(6-(4-(dimethylamino)piperidin-1-yl)pyridazin-3-yl)-9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1588958-88-6 N-(5-(4-(dimethylamino)piperidin-1-yl)pyridin-2-yl)-9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1588958-86-4 N-(5-(4-aminopiperidin-1-yl)pyridin-2-yl)-9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1588958-84-2 9-((1r,4r)-4-methylcyclohexyl)-N-(6-(piperazin-1-yl)pyridazin-3-yl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 

Relevant articles and documents

Electrochemical trifluoromethylation of aromatic compounds

It was shown that the current yield of the products of anodic trifluoromethylation of arenes correlates with the adsorptivity and the rate of electrooxidation of arenes on the surface of a platinum electrode.

Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent

The trifluoromethylation of iodoarenes was accomplished by use of a 2-trifluoromethylbenzimidazoline derivative as the trifluoromethylating reagent and a catalytic amount of Cu(I) in the presence of 2,2'-bipyridyl as the ligand. Through a mechanistic study, we found that the oxidative addition of the iodoarene to the Cu(I)–CF3 species is the rate-determining step.

NITRATION

The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.

Preparation method of substituted nitrobenzene compound

The invention discloses a preparation method of a substituted nitrobenzene compound. The method comprises the following steps: carrying out a decarboxylation reaction as shown below on a compound II under the action of alkali in a solvent at the temperature of 150 to 250 DEG C to obtain a compound I; the alkali is one or more of carbonates and bicarbonates of alkali metals. Compared with some metal-catalyzed decarboxylation methods, the preparation method of the substituted nitrobenzene compound has the advantages of simple operation, low production cost, convenient post-treatment and high yield, and more application values in industrial production.