Toluene → HCID 13983135, compound

HRID 477698Notes

Reaction equation

HRID 477698 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-ab65305474184d5083346f1309897ccc
Source dataset
uspto-grants-1989_12
Patent number
US04888426

Reaction notes

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