Tetrahydrofuran → HCID 13769708, compound

HRID 979942Notes

Reaction equation

HRID 979942 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][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]([CH2:25][CH2:26][NH:27][C:28]#[N:29])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[O:30]1C[CH2:33][CH2:32][CH2:31]1.OCC(=O)C.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][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[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][NH:27][C:28]3[O:30][CH:31]=[C:32]([CH3:33])[N:29]=3)[CH2:23][CH2:24]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8299HydroxyacetoneHCID 14798Sodium HydroxideHCID 20222935HCID 20222935, compound

Product 1

HCID 13769708HCID 13769708, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 1.95 parts of [2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-cyanamide, 45 parts of tetrahydrofuran and 50 parts of water was added a solution of 3.7 parts of 1-hydroxy-2-propanone in water (=50%). 5 Parts of a sodium hydroxide solution 2N were added dropwise. Upon completion, stirring was continued for 2 hours at room temperature. The reaction mixture was poured onto water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified 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 1.3 parts (6%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[(4-methyl-2-oxazolyl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 178.1° C. (compound 84).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionThe product was extracted with trichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-7d492b1265f24e1a93b10a2e1ccee9ba
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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