Dimethylformamide → HCID 131716976, compound

HRID 256663Notes

Reaction equation

HRID 256663 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[C:31]([CH2:32][CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[N:30][C:29]3[C:24]2=[N:25][CH:26]=[N:27][CH:28]=3)=[CH:18][CH:17]=1.[C:39](=[O:42])([O-:41])[O-].[Na+].[Na+].CN(C)[CH:47]=[O:48]>O>[C:47]([OH:48])(=[O:14])/[CH:38]=[CH:33]/[C:39]([OH:41])=[O:42].[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[C:31]([CH2:32][CH:33]3[CH2:34][CH2:35][N:36]([CH2:2][CH2:3][CH2:4][N:5]4[C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=5[NH:7][C:6]4=[O:14])[CH2:37][CH2:38]3)=[N:30][C:29]3[C:24]2=[N:25][CH:26]=[N:27][CH:28]=3)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 19785229HCID 19785229, compound

Product 1

HCID 131716976HCID 131716976, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.8 parts of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one, 2.7 parts of 9-[(4-fluorophenyl)methyl]-8-(4-piperidinylmethyl)-9H-purine, 1 part of sodium carbonate and 45 parts of N,N-dimethylformamide was stirred and heated overnight at 70° C. After cooling, the reaction mixture was poured into 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, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (E)-2-butenedioate salt in ethanol. The salt was filtered off and dried, yielding 2.85 parts (45.9%) of 1-[3-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]methyl]-1-piperidinyl]-propyl]-1,3-dihydro-2H-benzimidazol-2-one (E)-2-butenedioate(1:2); mp. 186.2° C. (compound 114).

Workup

  1. temperatureAfter cooling
  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. filtrationThe salt was filtered off
  11. customdried

Sources & evidence

ORD record
ord-11381ba911b74adbbf9dc922d57a2f87
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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