Acetic Anhydride → HCID 13653889, compound

HRID 280353Notes

Reaction equation

HRID 280353 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:19]3[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=3[N:17]=2)[CH2:11][CH2:10]1)=[O:5].[C:37](OC(=O)C)(=[O:39])[CH3:38].[OH-].[NH4+]>O>[C:37]([NH:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:19]3[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=3[N:17]=2)[CH2:11][CH2:10]1)=[O:5])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 13983254HCID 13983254, compound

Product 1

HCID 13653889HCID 13653889, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 7.7 parts of 2-amino-N-[2-[4-[[1-[(4-fluorophenyl)-methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]benzamide, 20 parts of acetic acid anhydride and 80 parts of water was stirred for 4 hours at 100° C. Water was added and the whole was alkalized with ammonium hydroxide. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 4-methyl-2-pentanone. The product was filtered off and recrystallized from acetonitrile, yielding 7.7 parts of 2-(acetylamino)-N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]benzamide; mp. 170.9° C. (compound 51).

Workup

  1. extractionThe product was extracted with trichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was crystallized from 4-methyl-2-pentanone
  6. filtrationThe product was filtered off
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-eb4c05ca694440399352fccfd29c29ee
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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