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Dimethylformamide → HCID 131716976, 화합물

HRID 256663
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HRID 256663 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

HCID 131716976HCID 131716976, 화합물수율 45.9%

시약·촉매·용매 1

HCID 962
Water
용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-11381ba911b74adbbf9dc922d57a2f87
출처 데이터셋
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05258380

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