Basic Information | Post buying leads | Suppliers | Cas Database |
Name |
MK-4305 |
EINECS | 685-109-7 |
CAS No. | 1030377-33-3 | Density | 1.419 g/cm3 |
PSA | 80.29000 | LogP | 4.11420 |
Solubility | N/A | Melting Point |
153℃ |
Formula | C23H23ClN6O2 | Boiling Point | 669.803 °C at 760 mmHg |
Molecular Weight | 450.928 | Flash Point | 358.884 °C |
Transport Information | N/A | Appearance | N/A |
Safety | Risk Codes | N/A | |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
MK-4305 |
Article Data | 23 |
2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid
5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
Suvorexant
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Reagent/catalyst; Solvent; Temperature; | 97% |
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 97% |
Stage #1: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 10℃; for 1h; Industry scale; Stage #2: 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole With triethylamine In dichloromethane at 15℃; for 1h; | 95% |
With triethylamine; chloroacetyl chloride In dichloromethane at 0 - 20℃; | 83% |
2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid
5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
C13H16ClN3O*C18H14O8
Suvorexant
Conditions | Yield |
---|---|
Stage #1: C13H16ClN3O*C18H14O8 With sodium hydroxide In dichloromethane; water at 20℃; for 1h; Stage #2: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 10℃; for 1h; Stage #3: 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole With triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 15℃; for 1h; optical yield given as %ee; | 95% |
2,5-dichloro-1,3-benzoxazole
1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone
Suvorexant
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 75℃; | 94% |
With triethylamine In N,N-dimethyl-formamide at 75℃; for 2h; | 93.02% |
With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Reagent/catalyst; Autoclave; Large scale; | 93.5% |
5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
Suvorexant
Conditions | Yield |
---|---|
Stage #1: 5-methyl-2-(1H-1,2,3-triazol-2-yl)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 10℃; for 1h; Stage #2: 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole With triethylamine In dichloromethane at -10 - -5℃; for 1h; | 92% |
2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid
5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride
Suvorexant
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h; | 91% |
With triethylamine; chloroacetyl chloride In dichloromethane at 0℃; | 88% |
Stage #1: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In Isopropyl acetate at 20 - 25℃; Inert atmosphere; Stage #2: 5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride With triethylamine In Isopropyl acetate; acetonitrile at 20 - 40℃; Product distribution / selectivity; | |
Stage #1: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride; Isopropyl acetate In N,N-dimethyl-formamide at 20 - 25℃; for 1h; Inert atmosphere; Stage #2: 5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride With Isopropyl acetate; potassium carbonate In water; N,N-dimethyl-formamide at 0 - 5℃; for 1.25h; Concentration; Solvent; Reagent/catalyst; | 14.4 g |
5-chloro-2-mercaptobenzoxazole
Suvorexant
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-mercaptobenzoxazole With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.916667h; Stage #2: (R)-(7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride With triethylamine In N,N-dimethyl-formamide at 20 - 37℃; for 0.5h; | 76% |
5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride
5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
A
Suvorexant
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 5 - 10℃; for 1.5h; | A 68% B n/a |
1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone
5-chloro-benzoxazole
Suvorexant
Conditions | Yield |
---|---|
With acetic acid In acetonitrile at 20℃; for 8h; Electrolysis; | 64.66% |
With oxygen; copper diacetate; acetic acid In acetonitrile at 70℃; for 4h; | 3.3 g |
2-iodoyl-5-methylbenzoic acid
Suvorexant
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: copper(l) iodide; potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 40 °C 1.2: 20 °C 2.1: sodium hydroxide / dichloromethane; water / 1 h / 20 °C 2.2: 1 h / 0 - 10 °C 2.3: 1 h / 0 - 15 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / tetrahydrofuran; water / 3 h / 22 - 25 °C / Inert atmosphere 1.2: 19 h / 21 - 23 °C / Inert atmosphere 2.1: oxalyl dichloride / Isopropyl acetate; N,N-dimethyl-formamide / 3 h / 20 - 25 °C / Inert atmosphere 3.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / copper(l) iodide / N,N-dimethyl-formamide; tetrahydrofuran / 40 - 65 °C / Industry scale 1.2: 20 °C 2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 10 °C / Industry scale 2.2: 1 h / 15 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide 2: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C 3: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 2 h / 75 °C View Scheme |
2-bromo-5-chlorobenzo[d]oxazole
Suvorexant
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: acetonitrile / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere 3: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere 4: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere 5: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: acetonitrile / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere 3: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere 4: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere 5: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere View Scheme |
The MK-4305 has CAS registry number 1030377-33-3. This chemical's molecular formula is C23H23ClN6O2 and molecular weight is 450.92. What's more, its systematic name is [(7R)-4-(5-Chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone.
Physical properties of MK-4305 are: (1)ACD/LogP: 3.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.266; (4)ACD/LogD (pH 7.4): 3.266; (5)ACD/BCF (pH 5.5): 178.763; (6)ACD/BCF (pH 7.4): 178.789; (7)ACD/KOC (pH 5.5): 1424.853; (8)ACD/KOC (pH 7.4): 1425.062; (9)#H bond acceptors: 8; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 80.29 Å2; (13)Index of Refraction: 1.703; (14)Molar Refractivity: 123.303 cm3; (15)Molar Volume: 317.803 cm3; (16)Polarizability: 48.881×10-24cm3; (17)Surface Tension: 55.831 dyne/cm; (18)Density: 1.419 g/cm3; (19)Flash Point: 358.884 °C; (20)Enthalpy of Vaporization: 98.428 kJ/mol; (21)Boiling Point: 669.803 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: Cc1ccc(c(c1)C(=O)N2CCN(CC[C@H]2C)c3nc4cc(ccc4o3)Cl)n5nccn5
(2)Std. InChI: InChI=1S/C23H23ClN6O2/c1-15-3-5-20(30-25-8-9-26-30)18(13-15)22(31)29-12-11-28(10-7-16(29)2)23-27-19-14-17(24)4-6-21(19)32-23/h3-6,8-9,13-14,16H,7,10-12H2,1-2H3/t16-/m1/s1
(3)Std. InChIKey: JYTNQNCOQXFQPK-MRXNPFEDSA-N