1,1'-Carbonyldiimidazole → HCID 14013072, compound

HRID 1904854Notes

Reaction equation

HRID 1904854 reaction equation
[NH2:1][C:2]1[CH:38]=[CH:37][CH:36]=[CH:35][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][C:18]2[N:22]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=2)[CH2:13][CH2:12]1)=[O:5].[C:39](N1C=CN=C1)(N1C=CN=C1)=[O:40]>O1CCCC1>[F:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:22]2[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=[C:18]2[CH2:17][CH:14]2[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH2:8][CH2:7][N:6]3[C:4](=[O:5])[C:3]4[C:2](=[CH:38][CH:37]=[CH:36][CH:35]=4)[NH:1][C:39]3=[O:40])[CH2:16][CH2:15]2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 14518067HCID 14518067, compound

Product 1

HCID 14013072HCID 14013072, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.3 parts of 2-amino-N-[4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]-butyl]benzamide, 3.2 parts of 1,1'-carbonylbis[1H-imidazole] and 180 parts of tetrahydrofuran was stirred and refluxed overnight. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using first a mixture of trichloromethane and methanol saturated with ammonia (97:3 by volume) and then a mixture of trichloromethane and methanol saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone, yielding 3.8 parts (35.5%) of 3-[4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]butyl]-2,4(1H,3H)-quinazolinedione; mp. 187.3° C. (489).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. customThe residue was purified by column chromatography over silica gel using first
  4. additiona mixture of trichloromethane and methanol saturated with ammonia (97:3 by volume)
  5. additiona mixture of trichloromethane and methanol saturated with ammonia (95:5 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from 2-propanone

Sources & evidence

ORD record
ord-6a67f94652a84092956a8f4f84f3ee34
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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