Acetone → HCID 14013324, compound

HRID 1904853Notes

Reaction equation

HRID 1904853 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]([O: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]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39].[CH3:43][C:44](=O)[CH3:45]>>[C:37]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39].[F:28][C:25]1[CH:26]=[CH:27][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[O: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)[NH:1][C:44]3([CH3:45])[CH3:43])[CH2:10][CH2:11]2)=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 971Oxalic AcidHCID 14013329HCID 14013329, compound

Product 1

HCID 14013324HCID 14013324, compoundYield 77%

Procedure

A mixture of 5 parts of 2-amino-N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]oxy]-1-piperidinyl]ethyl]-benzamide, 80 parts of 2-propanone and 1.9 parts of ethanedioic acid was stirred for 1 hour at reflux temperature. After cooling, the product was filtered off and dried, yielding 4.8 parts (77%) of 3-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]oxy]-1-piperidinyl]ethyl]-2,3-dihydro-2,2-dimethyl-4(1H)-quinazolinone ethanedioate (1:1); mp. 166.5° C. (485).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-cb527ff03a234b30a0c30ededf510154
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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