2-Amino-5-(methylsulfanyl)benzoic acid → 3-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-6-(methylthio)-4(3H)-quinazolinone

HRID 477694노트

반응식

HRID 477694 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[N:23]=[C:22]2[NH:30][CH:31]2[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][NH:39][CH:40]=O)[CH2:33][CH2:32]2)=[CH:16][CH:15]=1>>[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[N:23]=[C:22]2[NH:30][CH:31]2[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][N:39]3[C:4](=[O:6])[C:3]4[C:2](=[CH:10][CH:9]=[C:8]([S:11][CH3:12])[CH:7]=4)[N:1]=[CH:40]3)[CH2:33][CH2:32]2)=[CH:16][CH:15]=1

참가 물질

3

반응물 2

HCID 127132522-Amino-5-(methylsulfanyl)benzoic acidHCID 13653885N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]formamide

생성물 1

HCID 139831233-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-6-(methylthio)-4(3H)-quinazolinone수율 41.5%

실험 절차

A mixture of 3.7 parts of 2-amino-5-(methylthio)benzoic acid and 8.9 parts of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]formamide was stirred for 5 hours at 150°-160° C. The whole 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 a mixture of 1,1'-oxybisethane and acetonitrile. The product was filtered off and dried, yielding 4.5 parts (41.5%) of 3-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-6-(methylthio)-4(3H)-quinazolinone; mp. 101.4° C. (compound 138).

후처리

  1. customThe whole was purified by column chromatography over silica gel using
  2. additiona mixture of trichloromethane and methanol
  3. customThe pure fractions were collected
  4. customthe eluent was evaporated
  5. customThe residue was crystallized from a mixture of 1,1'-oxybisethane and acetonitrile
  6. filtrationThe product was filtered off
  7. customdried

출처 및 근거

ORD 기록
ord-1367af3eb6ee47ce9ea9bfd4d619788c
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04888426

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