Sodium Carbonate → N,N-dimethyl-alpha,alpha-diphenyl-4-[[9-(2-pyridinylmethyl)-9H-purin-8-yl]amino]-1-piperidinebutanamide

HRID 2248818노트

반응식

HRID 2248818 반응식
[Br-].[C:2]1([C:8]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][O:10][C:9]2=[N+:13]([CH3:15])[CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:22]1[CH2:27][CH2:26][CH:25]([NH:28][C:29]2[N:30]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=3)[C:31]3[C:36]([N:37]=2)=[CH:35][N:34]=[CH:33][N:32]=3)[CH2:24][CH2:23]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[CH3:14][N:13]([CH3:15])[C:9](=[O:10])[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:12][CH2:11][N:22]1[CH2:23][CH2:24][CH:25]([NH:28][C:29]2[N:30]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=3)[C:31]3[C:36]([N:37]=2)=[CH:35][N:34]=[CH:33][N:32]=3)[CH2:26][CH2:27]1

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 2723589(Dihydro-3,3-diphenyl-3H-furan-2-ylidene)dimethylammonium bromideHCID 19785321N-(4-piperidinyl)-9-(2-pyridinylmethyl)-9H-purin-8-amine

생성물 1

HCID 53782909N,N-dimethyl-alpha,alpha-diphenyl-4-[[9-(2-pyridinylmethyl)-9H-purin-8-yl]amino]-1-piperidinebutanamide수율 71%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of 3.46 parts of N-(dihydro-3,3-diphenyl-2(3H)-furanylidene)-N-methylmethanaminium bromide, 3.1 parts of N-(4-piperidinyl)-9-(2-pyridinylmethyl)-9H-purin-8-amine, 1.5 parts of sodium carbonate and 45 parts of N,N-dimethylacetamide was stirred overnight at 80° C. after cooling, the reaction mixture was poured into water and the product was extracted with 4-methyl-2-pentanone. 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 crystallized from acetonitrile. The product was filtered off and dried, yielding 4.1 parts (71%) of N,N-dimethyl-α,α-diphenyl-4-[[9-(2-pyridinylmethyl)-9H-purin-8-yl]amino]-1-piperidinebutanamide; mp. 191.6° C. (compound 122).

후처리

  1. temperatureafter cooling
  2. extractionthe product was extracted with 4-methyl-2-pentanone
  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
  11. filtrationThe product was filtered off
  12. customdried

출처 및 근거

ORD 기록
ord-f439600a495c401ca922974c90688a20
출처 데이터셋
uspto-grants-1991_08
특허 번호
US05041448

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