Methyl chloroformate → HCID 86732380, compound

HRID 517257Notes

Reaction equation

HRID 517257 reaction equation
[O:1]=[C:2]1[NH:11][CH:10]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:20])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1.[H-].[Na+].Cl[C:34]([O:36][CH3:37])=[O:35]>O1CCCC1.O.CN(C)C=O>[C:16]([C:15]1[CH:14]=[CH:13][C:12]([CH:10]2[C:9]3[C:8](=[O:20])[CH2:7][CH2:6][CH2:5][C:4]=3[N:3]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=3)[C:2](=[O:1])[N:11]2[C:34]([O:36][CH3:37])=[O:35])=[CH:19][CH:18]=1)#[N:17]

Participants

7

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydride2×HCID 86732326HCID 86732326, compound

Product 1

HCID 86732380HCID 86732380, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile (example 1, 60 mg, 0.146 mmol) in tetrahydrofuran (0.8 mL) is added to a suspension of sodium hydride (60% in mineral oil, 7 mg, 0.17 mmol) in tetrahydrofuran (0.5 mL). After 20 min methyl chloroformate (11 μL, 0.15 mmol) is added and the mixture is stirred at room temperature over night. Another portion of sodium hydride (60% in mineral oil, 3 mg, 0.07 mmol) is added. After 2 h, the mixture is diluted with water and N,N-dimethylformamide and then purified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 8 mg; ESI mass spectrum [M+H]+=470, Retention time HPLC: 1.14 min (V011_S01).

Workup

  1. custompurified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  2. custom1.14 min (V011_S01)

Sources & evidence

ORD record
ord-6ff2b3336fea460fa3337427b231840b
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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