Acetic Anhydride → HCID 14013068, compound

HRID 1904852Notes

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]([CH2:15][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]([O:40][C:41](=[O:43])[CH3:42])(=O)[CH3:38].[OH-:44].[NH4+]>O>[C:41]([OH:40])(=[O:43])/[CH:42]=[CH:3]/[C:4]([OH:5])=[O:44].[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:20]2[C:19]3[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=3[N:17]=[C:16]2[CH2:15][CH:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][N:6]3[C:4](=[O:5])[C:3]4[C:2](=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:1]=[C:37]3[CH3:38])[CH2:10][CH2:11]2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4 parts of 2-amino-N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl)methyl]-1-piperidinyl]ethyl]benzamide, 20 parts of acetic acid anhydride and 40 parts of water was stirred and heated overnight at 120° C. After cooling, ice water was added. The whole was treated with ammonium hydroxide. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was converted into the (E)-2-butenedioate salt in ethanol. The salt was filtered off and dried, yielding 3.7 parts (72%) of 3-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]-2-methyl-4(3H)-quinazolinone (E)-2-butenedioate (1:1); mp. 210.3° C. (481).

Workup

temperatureAfter cooling
extractionThe product was extracted with dichloromethane
customThe extract was dried
filtrationfiltered
customevaporated
filtrationThe salt was filtered off
customdried

Sources & evidence

ORD record: ord-ef8398e55e2646d7849509357bf737b3
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04839374

Reaction notes

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