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1030377-33-3

Basic Information
CAS No.: 1030377-33-3
Name: MK-4305
Molecular Structure:
Molecular Structure of 1030377-33-3 (MK-4305)
Formula: C23H23ClN6O2
Molecular Weight: 450.92
Synonyms: MK-4305
EINECS: 685-109-7
Density: 1.419 g/cm3
Melting Point: 153℃
Boiling Point: 669.803 °C at 760 mmHg
Flash Point: 358.884 °C
Solubility:
Appearance:
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 80.29000
LogP: 4.11420
Synthetic route
956317-36-5

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid

1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

1030377-33-3

Suvorexant

Conditions
ConditionsYield
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%
956317-36-5

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid

1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

1276666-14-8

C13H16ClN3O*C18H14O8

1030377-33-3

Suvorexant

Conditions
ConditionsYield
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%
3621-81-6

2,5-dichloro-1,3-benzoxazole

1030377-32-2

1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone

1030377-33-3

Suvorexant

Conditions
ConditionsYield
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%
1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

5-methyl-2-(1H-1,2,3-triazol-2-yl)benzoic acid

1030377-33-3

Suvorexant

Conditions
ConditionsYield
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%
956317-36-5

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid

1266664-66-7

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride

1030377-33-3

Suvorexant

Conditions
ConditionsYield
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
22876-19-3

5-chloro-2-mercaptobenzoxazole

(R)-(7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride

1030377-33-3

Suvorexant

Conditions
ConditionsYield
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%
1104546-96-4

5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride

1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

A

1030377-33-3

Suvorexant

B

C23H23ClN6O2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 5 - 10℃; for 1.5h;A 68%
B n/a
1030377-32-2

1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone

17200-29-2

5-chloro-benzoxazole

1030377-33-3

Suvorexant

Conditions
ConditionsYield
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
52548-14-8

2-iodoyl-5-methylbenzoic acid

1030377-33-3

Suvorexant

Conditions
ConditionsYield
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
1251033-26-7

2-bromo-5-chlorobenzo[d]oxazole

1030377-33-3

Suvorexant

Conditions
ConditionsYield
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
1356342-15-8

2-[(5-chloro-1,3-benzoxazol-2-yl)amino]ethanol

1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
2: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
3: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
4: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere
2: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
3: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
4: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
1.2: 1.25 h / 0 - 10 °C
2.1: isopropylamine hydrochloride; triethanolamine; pyridoxal 5'-phosphate; isopropylamine mesylate / water; dimethyl sulfoxide / 11 h / 40 °C / pH 8.5 / Enzymatic reaction
3.1: oxalyl dichloride; Isopropyl acetate / N,N-dimethyl-formamide / 1 h / 20 - 25 °C / Inert atmosphere
3.2: 1.25 h / 0 - 5 °C
View Scheme
1383717-09-6

C13H15ClN2O3

1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
2: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
3: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
1383717-11-0

methanesulfonic acid 2-[(5-chloro-benzooxazol-2-yl)-(3-oxo-butyl)amino]ethyl ester

1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
2: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: isopropylamine hydrochloride; triethanolamine; pyridoxal 5'-phosphate; isopropylamine mesylate / water; dimethyl sulfoxide / 11 h / 40 °C / pH 8.5 / Enzymatic reaction
2.1: oxalyl dichloride; Isopropyl acetate / N,N-dimethyl-formamide / 1 h / 20 - 25 °C / Inert atmosphere
2.2: 1.25 h / 0 - 5 °C
View Scheme
1104546-96-4

5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride

1266664-66-7

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride

1030377-33-3

Suvorexant

Conditions
ConditionsYield
With potassium carbonate In Isopropyl acetate; water at 0℃; for 1.25h; Inert atmosphere;14.4 g
95-85-2

2-hydroxy-5-chloro-aniline

1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 60 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.83 h / -25 - -15 °C / Inert atmosphere
2.2: 3.33 h / -20 - -15 °C / Inert atmosphere
3.1: acetonitrile / Inert atmosphere
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere
5.1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
6.1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
7.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 60 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.83 h / -25 - -15 °C / Inert atmosphere
2.2: 3.33 h / -20 - -15 °C / Inert atmosphere
3.1: acetonitrile / Inert atmosphere
4.1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
5.1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
6.1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
7.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: water; methanol / 0 - 5 °C / Industry scale
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1.75 h / 25 °C / Industry scale
2.2: 2.5 h / 10 - 20 °C
2.3: 10 h / 20 °C
3.1: hydrogenchloride; water / 10 h / 20 - 30 °C
3.2: 35 °C / pH > 10
3.3: 24 h / -5 °C / Inert atmosphere
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 10 °C / Industry scale
4.2: 1 h / 15 °C
View Scheme
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    5-Chloro-2-[(5R)-5-methyl-4-[5-methyl-2-(2H-1,2,3-triazol-2-yl)-benzoyl]-1,4-diazepan-1-yl]-1,3-benzoxazole

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Specification

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