Acetic Anhydride → 1-acetyl-N-{4-[(2-{[2-fluoro-5-(trifluoro methyl)phenyl]amino}-1-methyl-1H-benzimidazol-5-yl)oxy]pyridin-2-yl}piperidine-4-carboxamide

HRID 30788Notes

Reaction equation

HRID 30788 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]1[N:17]([CH3:18])[C:16]2[CH:19]=[CH:20][C:21]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([CH:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)=[O:32])[CH:25]=3)=[CH:22][C:15]=2[N:14]=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>O1CCOCC1>[C:39]([N:36]1[CH2:37][CH2:38][CH:33]([C:31]([NH:30][C:26]2[CH:25]=[C:24]([O:23][C:21]3[CH:20]=[CH:19][C:16]4[N:17]([CH3:18])[C:13]([NH:12][C:3]5[CH:4]=[C:5]([C:8]([F:9])([F:10])[F:11])[CH:6]=[CH:7][C:2]=5[F:1])=[N:14][C:15]=4[CH:22]=3)[CH:29]=[CH:28][N:27]=2)=[O:32])[CH2:34][CH2:35]1)(=[O:41])[CH3:40]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 59790243N-{4-[(2-{[2-fluoro-5-(trifluoromethyl)phenyl]amino}-1-methyl-1H-benzimidazol-5-yl)oxy]pyridin-2-yl}piperidine-4-carboxamide

Product 1

HCID 597899631-acetyl-N-{4-[(2-{[2-fluoro-5-(trifluoro methyl)phenyl]amino}-1-methyl-1H-benzimidazol-5-yl)oxy]pyridin-2-yl}piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To N-{4-[(2-{[2-fluoro-5-(trifluoromethyl)phenyl]amino}-1-methyl-1H-benzimidazol-5-yl)oxy]pyridin-2-yl}piperidine-4-carboxamide (1 eq) in dioxane and N,N-disopropylethylamine (2 eq) was added acetic anhydride (1 eq) and the resulting mixture was stirred for 1 h. 1-acetyl-N-{4-[(2-{[2-fluoro-5-(trifluoromethyl)phenyl]amino}-1-methyl-1H-benzimidazol-5-yl)oxy]pyridin-2-yl}piperidine-4-carboxamide thus formed was purified by preparative chromatography. MS: MH+=571.5.

Sources & evidence

ORD record
ord-3cbbaf8468264e0d8a8cec00c330ffa1
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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