Ethyl chloroformate → HCID 178473431, compound

HRID 1507470Notes

Reaction equation

HRID 1507470 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[N:10][C:11]([C:13]2[CH:17]=[C:16]([CH3:18])[O:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[O:12])[CH2:3]1.C(N(C(C)C)CC)(C)C.[CH2:40]([O:42][C:43](Cl)=[O:44])[CH3:41]>ClCCl>[F:30][C:26]1[CH:25]=[C:24]([NH:23][C:9](=[N:10][C:11]([C:13]2[CH:17]=[C:16]([CH3:18])[O:15][C:14]=2[C:19]([F:20])([F:21])[F:22])=[O:12])[NH:8][CH:4]2[CH2:5][CH2:6][CH2:7][CH:2]([NH:1][C:43](=[O:44])[O:42][CH2:40][CH3:41])[CH2:3]2)[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 178427206HCID 178427206, compound

Product 1

HCID 178473431HCID 178473431, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(((3-Aminocyclohexyl)amino)((3-fluorophenyl)amino)methylene)-5-methyl-2-(trifluoromethyl)furan-3-carboxamide (0.150 g, 0.240 mmol) and diisopropylethyl amine (DIEA) (0.037 g, 0.288 mmol) were dissolved in dichloromethane (DCM) (5 mL). Ethylchloroformate (0.032 g, 0.288 mmol) was added and the reaction mixture was stirred for one hour. Then, the solvents were evaporated under a stream of nitrogen and the resulting residue purified by column chromatography (0-40%, hexanes:EtOAc) to yield 123 mg of the title compound (70% yield). LCMS (ESI): calc.=498; obs. M+H=499.5.

Workup

  1. customThen, the solvents were evaporated under a stream of nitrogen
  2. customthe resulting residue purified by column chromatography (0-40%, hexanes:EtOAc)

Sources & evidence

ORD record
ord-4144b8089a86454d99bdaf61eb657fe2
Source dataset
uspto-grants-2015_12
Patent number
US09221814B2

Reaction notes

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