N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine → HCID 178526944, compound

HRID 845793Notes

Reaction equation

HRID 845793 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10](=[O:17])[N:11]=[C:12](SC)[NH:13][CH:14]=2)=[CH:4][CH:3]=1.[NH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:28]2[N:32]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[C:31]3[CH:41]=[CH:42][CH:43]=[CH:44][C:30]=3[N:29]=2)[CH2:23][CH2:22]1>ClC(Cl)Cl>[OH2:17].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10](=[O:17])[N:11]=[C:12]([NH:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([NH:27][C:28]4[N:32]([CH2:33][C:34]5[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=5)[C:31]5[CH:41]=[CH:42][CH:43]=[CH:44][C:30]=5[N:29]=4)[CH2:23][CH2:22]3)[NH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12891741N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amineHCID 178503535HCID 178503535, compound

Product 1

HCID 178526944HCID 178526944, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2.7 parts of 5-[(4-chlorophenyl)methyl]-2-(methylthio)-4(1H)-pyrimidinone and 3.67 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol -2-amine was stirred and heated for 4 hours at 140° C. The reaction mixture was cooled and taken up in trichloromethane. The solution was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume), saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was suspended in 1,1'-oxybisethane, yielding 4.5 parts (76.8%) of 5-[(4-chlorophenyl)methyl]-2-[[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]amino]-4(1H)-pyrimidinone monohydrate; mp. 150.6°-158.7° C. (compound 85).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe solution was purified by column-chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol (96:4 by volume)
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated

Sources & evidence

ORD record
ord-fda133b88aa546eaaec18836781ab3ec
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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