Toluene → HCID 13983135, compound

HRID 1493949Notes

Reaction equation

HRID 1493949 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].Br[CH2:8][C:9](=O)[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:22]3[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=3[N:20]=2)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].CC1C=CC=CC=1>O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:23]2[C:22]3[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=3[N:20]=[C:19]2[NH:18][CH:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][C:9]3[N:6]=[C:2]4[N:3]([CH:8]=3)[CH:4]=[CH:5][S:1]4)[CH2:17][CH2:16]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 21552-AminothiazoleHCID 10340Sodium CarbonateHCID 14835302HCID 14835302, compound

Product 1

HCID 13983135HCID 13983135, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2 parts of 2-thiazolamine, 12.7 parts of 1-bromo-4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-2-butanone, 6.4 parts of sodium carbonate and 135 parts of methylbenzene was stirred and refluxed for 3 hours using a water separator. The whole was filtered and the filtrate was evaporated. The residue was purified twice by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 0.5 parts (5.3%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-(imidazo[2,1-b]thiazol-6-yl)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 222.7° C. (compound 149).

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe whole was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified twice by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-3bd5bff2008e40dcbd362cd1306cb929
Source dataset
uspto-grants-1991_06
Patent number
US05025014

Reaction notes

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