Dimethylformamide → ethyl 4-[[1-[(2-methyl-5-oxazolyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate

HRID 1197822Notes

Reaction equation

HRID 1197822 reaction equation
Br[CH2:2][C:3]1[O:7][C:6]([CH3:8])=[N:5][CH:4]=1.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[CH3:8][C:6]1[O:7][C:3]([CH2:2][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]2)=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl esterHCID 128087865-(Bromomethyl)-2-methyloxazole

Product 1

HCID 19105060ethyl 4-[[1-[(2-methyl-5-oxazolyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylateYield 11.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 23 parts of 5-(bromomethyl)-2-methyloxazole, 57.6 parts of ethyl 4-[(1H-benzimidazol-2-yl)amino]-1-piperidinecarboxylate, 26.5 parts of sodium carbonate and 470 parts of N,N-dimethylformamide was stirred for 18 hours at 80° C. The reaction mixture was poured into water and the whole was extracted with 4-methyl-2-pentanone. The extract was washed with water, dried, filtered and evaporated. The residue was stirred in acetonitrile. The precipitate was filtered off and the filtrate was evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 90:10). The eluent of the desired fraction was evaporated, yielding 6 parts (11.2%) of ethyl 4-[[1-[(2-methyl-5-oxazolyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate (comp. 2).

Workup

  1. extractionthe whole was extracted with 4-methyl-2-pentanone
  2. washThe extract was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. stirringThe residue was stirred in acetonitrile
  7. filtrationThe precipitate was filtered off
  8. customthe filtrate was evaporated
  9. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 90:10)
  10. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-a9d81ef28dee4c71a3f4be4cfe4f67ab
Source dataset
uspto-grants-1994_01
Patent number
US05278165

Reaction notes

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