Acetic Anhydride → HCID 86713979, compound

HRID 514255Notes

Reaction equation

HRID 514255 reaction equation
F[C:2](F)(F)[C:3]([O-])=[O:4].[Cl:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:20](=[O:37])[NH:21][CH:22]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[C:23]([F:26])([F:25])[F:24])[N:15]2[CH2:18][CH3:19])=[CH:11][C:10]=1[CH2:38][NH3+:39].C(N(CC)CC)C.C(OC(=O)C)(=O)C.C(OCC)(=O)C>CN(C)C1C=CN=CC=1.ClCCl>[C:3]([NH:39][CH2:38][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:9]=1[Cl:8])[N:15]([CH2:18][CH3:19])[C:14]([C:20]([NH:21][CH:22]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:35])[F:36])[CH:28]=1)[C:23]([F:25])([F:24])[F:26])=[O:37])=[CH:13]2)(=[O:4])[CH3:2]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86713977HCID 86713977, compound

Product 1

HCID 86713979HCID 86713979, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

At 0° C., [6-chloro-1-ethyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indol-5-yl]methanaminium trifluoroacetate (0.07 g, 0.15 mmol), triethylamine (0.036 g, 0.36 mmol) and N,N-dimethylpyridin-4-amine (0.002 g, 0.12 mmol) were initially charged in dichloromethane (1 ml). Acetic anhydride (0.021 g, 0.21 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic phase was washed successively with water, saturated ammonium chloride solution and saturated sodium hydrogencarbonate solution. The organic phase was dried over sodium sulphate and the solvent was removed under reduced pressure. 0.06 g (98% of theory) of 5-(acetamidomethyl)-6-chloro-1-ethyl-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2-carboxamide was obtained.

Workup

  1. washthe organic phase was washed successively with water, saturated ammonium chloride solution and saturated sodium hydrogencarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-50fd387593b04ca7b6a823b6dd972eb3
Source dataset
uspto-grants-2015_08
Patent number
US09107411B2

Reaction notes

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