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1268524-70-4

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CAS No.: 1268524-70-4
Name: (S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-triMethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate
Article Data: 46
Molecular Structure:
Molecular Structure of 1268524-70-4 ((S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-triMethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate)
Formula: C23H25ClN4O2S
Molecular Weight: 456.996
Synonyms: (S)-(+)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate;
Density: 1.3±0.1 g/cm3
Boiling Point: 610.4±65.0 °C at 760 mmHg
Flash Point: 322.9±34.3 °C
PSA: 97.61000
LogP: 4.96690
Related products
Synthetic route
1268524-67-9

(S)-tert-butyl 2-(5-(4-chlorophenyl)-6,7-dimethyl-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate

1068-57-1

acetic acid hydrazide

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Stage #1: tert-butyl (S)-2-(5-(4-chlorophenyl)-6,7-dimethyl-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate With potassium tert-butylate In tetrahydrofuran at -78 - 23℃; for 0.5h;
Stage #2: With diethyl chlorophosphate In tetrahydrofuran at -10℃; for 0.75h;
Stage #3: acetic acid hydrazide In tetrahydrofuran; butan-1-ol at 23 - 90℃; for 2h;		92%
Stage #1: tert-butyl (S)-2-(5-(4-chlorophenyl)-6,7-dimethyl-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate With potassium tert-butylate In tetrahydrofuran at -78 - -10℃; for 0.5h;
Stage #2: With chlorophosphoric acid diphenyl ester In tetrahydrofuran at -78 - -40℃; for 0.75h;
Stage #3: acetic acid hydrazide Further stages;		60.2%
With potassium tert-butylate; diethyl chlorophosphate In tetrahydrofuran
Stage #1: tert-butyl (S)-2-(5-(4-chlorophenyl)-6,7-dimethyl-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate In tetrahydrofuran; toluene at -40℃; for 1h;
Stage #2: With chlorophosphoric acid diphenyl ester In tetrahydrofuran; toluene at -10℃; for 2.3h;
Stage #3: acetic acid hydrazide In tetrahydrofuran; toluene at 20 - 80℃; for 2.5h; Reagent/catalyst; Temperature; Solvent;
1445-45-0

Trimethyl orthoacetate

C21H23ClN2O2S2

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Stage #1: C21H23ClN2O2S2 With hydrazine hydrate In tetrahydrofuran at 23℃; for 1h;
Stage #2: Trimethyl orthoacetate In toluene at 120℃; for 2h;		85%
50508-66-2

(2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) / N,N-dimethyl-formamide / 16 h / 23 °C
2.1: piperidine / N,N-dimethyl-formamide / 0.5 h / 23 °C
3.1: silica gel / ethanol / 3 h / 90 °C
4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -78 - 23 °C
4.2: 0.75 h / -10 °C
4.3: 2 h / 23 - 90 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) / N,N-dimethyl-formamide / 16 h / 23 °C
2.1: piperidine / N,N-dimethyl-formamide / 0.5 h / 23 °C
3.1: silica gel / ethanol / 3 h / 90 °C
4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -78 - 23 °C
4.2: 0.75 h / -10 °C
4.3: 2 h / 23 - 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / 23 °C
1.2: 16 h / 23 °C
2.1: piperidine / N,N-dimethyl-formamide / 0.5 h / 23 °C
3.1: acetic acid / ethanol / 0.5 h / 85 °C
4.1: tetraphosphorus decasulfide; sodium hydrogencarbonate / tetrahydrofuran / 16 h / 90 °C
5.1: hydrazine hydrate / tetrahydrofuran / 1 h / 23 °C
5.2: 2 h / 120 °C
View Scheme
4640-66-8

p-chlorobenzoylacetonitrile

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: morpholine; sulfur / ethanol / 12 h / 23 - 70 °C
2.1: N-ethyl-N,N-diisopropylamine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) / N,N-dimethyl-formamide / 16 h / 23 °C
3.1: piperidine / N,N-dimethyl-formamide / 0.5 h / 23 °C
4.1: silica gel / ethanol / 3 h / 90 °C
5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -78 - 23 °C
5.2: 0.75 h / -10 °C
5.3: 2 h / 23 - 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: morpholine; sulfur / ethanol / 12 h / 23 - 70 °C
2.1: N-ethyl-N,N-diisopropylamine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) / N,N-dimethyl-formamide / 16 h / 23 °C
3.1: piperidine / N,N-dimethyl-formamide / 0.5 h / 23 °C
4.1: silica gel / ethanol / 3 h / 90 °C
5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -78 - 23 °C
5.2: 0.75 h / -10 °C
5.3: 2 h / 23 - 90 °C
View Scheme
Multi-step reaction with 6 steps
1.1: morpholine; sulfur / ethanol / 12 h / 25 °C
2.1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / 23 °C
2.2: 16 h / 23 °C
3.1: piperidine / N,N-dimethyl-formamide / 0.5 h / 23 °C
4.1: acetic acid / ethanol / 0.5 h / 85 °C
5.1: tetraphosphorus decasulfide; sodium hydrogencarbonate / tetrahydrofuran / 16 h / 90 °C
6.1: hydrazine hydrate / tetrahydrofuran / 1 h / 23 °C
6.2: 2 h / 120 °C
View Scheme
1268524-66-8

(S)-tert-butyl-3-amino-4-((3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)amino)-4-oxobutanoate

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: silica gel / ethanol / 3 h / 90 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -78 - 23 °C
2.2: 0.75 h / -10 °C
2.3: 2 h / 23 - 90 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid / ethanol / 0.5 h / 85 °C
2.1: tetraphosphorus decasulfide; sodium hydrogencarbonate / tetrahydrofuran / 16 h / 90 °C
3.1: hydrazine hydrate / tetrahydrofuran / 1 h / 23 °C
3.2: 2 h / 120 °C
View Scheme
Multi-step reaction with 2 steps
1: silica gel / toluene
2: potassium tert-butylate; diethyl chlorophosphate / tetrahydrofuran
View Scheme

tert-butyl-3-amino-4-((3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)amino)-4-oxobutanoate

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: acetic acid / ethanol / 0.5 h / 85 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -78 - 23 °C
2.2: 0.75 h / -10 °C
2.3: 2 h / 23 - 90 °C
View Scheme
1268524-67-9

(S)-tert-butyl 2-(5-(4-chlorophenyl)-6,7-dimethyl-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate

A

1268524-71-5

(-)-JQ1

B

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -78 - -10 °C
1.2: 0.75 h / -78 - -10 °C
2.1: tetrahydrofuran; butan-1-ol / 2 h / 20 - 90 °C
View Scheme

(R)-tert-butyl 2-(5-(4-chlorophenyl)-6,7-dimethyl-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tetraphosphorus decasulfide; sodium hydrogencarbonate / tetrahydrofuran / 16 h / 90 °C
2.1: hydrazine hydrate / tetrahydrofuran / 1 h / 23 °C
2.2: 2 h / 120 °C
View Scheme
873-76-7

para-Chlorobenzyl alcohol

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: copper dichloride; potassium hydroxide; oxygen / N,N-dimethyl acetamide / 12 h / 25 °C
2.1: morpholine; sulfur / ethanol / 12 h / 25 °C
3.1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / 23 °C
3.2: 16 h / 23 °C
4.1: piperidine / N,N-dimethyl-formamide / 0.5 h / 23 °C
5.1: acetic acid / ethanol / 0.5 h / 85 °C
6.1: tetraphosphorus decasulfide; sodium hydrogencarbonate / tetrahydrofuran / 16 h / 90 °C
7.1: hydrazine hydrate / tetrahydrofuran / 1 h / 23 °C
7.2: 2 h / 120 °C
View Scheme

C9H7NOS

1268524-70-4

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: morpholine; sulfur / ethanol
2: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
3: piperidine / N,N-dimethyl-formamide
4: silica gel / toluene
5: potassium tert-butylate; diethyl chlorophosphate / tetrahydrofuran
View Scheme
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Specification

The (+)-JQ-1, with the CAS registry number 1268524-70-4, is also known as 6H-Thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid, 4-(4-chlorophenyl)-2,3,9-trimethyl-, 1,1-dimethylethyl ester, (6S)-. This chemical's molecular formula is C23H25ClN4O2S and molecular weight is 456.99.

Physical properties of (+)-JQ-1 are: (1)ACD/LogP: 4.49±1.44; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.49; (4)ACD/LogD (pH 7.4): 4.49; (5)ACD/BCF (pH 5.5): 1507.25; (6)ACD/BCF (pH 7.4): 1508.63; (7)ACD/KOC (pH 5.5): 6552.81; (8)ACD/KOC (pH 7.4): 6558.84; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 97.61 Å2; (13)Index of Refraction: 1.657; (14)Molar Refractivity: 125.5±0.5 cm3; (15)Molar Volume: 341.2±7.0 cm3; (16)Polarizability: 49.8±0.5×10-24cm3; (17)Surface Tension: 46.2±7.0 dyne/cm; (18)Density: 1.3±0.1 g/cm3; (19)Flash Point: 322.9±34.3 °C; (20)Enthalpy of Vaporization: 90.6±3.0 kJ/mol; (21)Boiling Point: 610.4±65.0 °C at 760 mmHg; (22)Vapour Pressure: 0.0±1.7 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1c(sc-2c1C(=N[C@H](c3n2c(nn3)C)CC(=O)OC(C)(C)C)c4ccc(cc4)Cl)C
(2)Std. InChI: InChI=1S/C23H25ClN4O2S/c1-12-13(2)31-22-19(12)20(15-7-9-16(24)10-8-15)25-17(11-18(29)30-23(4,5)6)21-27-26-14(3)28(21)22/h7-10,17H,11H2,1-6H3/t17-/m0/s1
(3)Std. InChIKey: DNVXATUJJDPFDM-KRWDZBQOSA-N