Formic Acid → HCID 13983122, compound

HRID 2309534Notes

Reaction equation

HRID 2309534 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].[CH:37](O)=O>CC1C=CC=CC=1>[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[CH2:13][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]=[CH:37]3)[CH2:10][CH2:11]2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 13983254HCID 13983254, compound

Product 1

HCID 13983122HCID 13983122, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4.86 parts of 2-amino-N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]benzamide, 1.4 parts of formic acid and 45 parts of methylbenzene was stirred and refluxed overnight. The reaction mixture was evaporated and the residue was taken up in trichloromethane, water and ammonium hydroxide. The organic phase was separated, dried, filtered and evaporated. The residue was crystallized from acetonitrile, yielding 3.6 parts (73%) of 3-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-4(3H)-quinazolinone; mp. 190.6° C. (compound 137).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. customThe organic phase was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-f04dff4f8f7a44db98ca26f77d5faeda
Source dataset
uspto-grants-1987_09
Patent number
US04695569

Reaction notes

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