1,1'-Carbonyldiimidazole → HCID 13983116, compound

HRID 1493940Notes

Reaction equation

HRID 1493940 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][C:34]([S:37][CH3:38])=[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:39](N1C=CN=C1)(N1C=CN=C1)=[O:40]>O1CCCC1>[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[NH:15][CH:12]2[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][N:6]3[C:4](=[O:5])[C:3]4[C:2](=[CH:36][CH:35]=[C:34]([S:37][CH3:38])[CH:33]=4)[NH:1][C:39]3=[O:40])[CH2:14][CH2:13]2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 13983263HCID 13983263, compound

Product 1

HCID 13983116HCID 13983116, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6 parts of 2-amino-N-[2-[4-[[1-[(4-fluorophenyl)-methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-5-(methylthio)benzamide, 1.78 parts of 1,1'-carbonylbis[1H-imidazole] and 90 parts of tetrahydrofuran was stirred and refluxed overnight. The reaction mixture was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 5.2 parts (85%) of 3-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-6-(methylthio)-2,4(1H,3H)-quinazolinedione; mp. 238° C. (compound 126).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. customThe residue was crystallized from acetonitrile
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-78fcdd9ba7704277b0dd45586cab2dbc
Source dataset
uspto-grants-1991_06
Patent number
US05025014

Reaction notes

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