rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl ester → HCID 58312626, 화합물

HRID 527503

반응식

HRID 527503 반응식
NC1C(C2C=CC(Cl)=C(Cl)C=2)CN(C(C2CCN(C(C3(C)CC3)=O)CC2)=O)C1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37](=[O:68])[N:38]([C@H:41]2[C@H:45]([C:46]3[CH:51]=[CH:50][C:49]([Cl:52])=[C:48](Cl)[CH:47]=3)[CH2:44][N:43](C(C3CCN(C(C4(C)CC4)=O)CC3)=O)[CH2:42]2)[CH2:39][CH3:40])=[CH:32][CH:31]=1>>[F:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37](=[O:68])[N:38]([C@H:41]2[C@H:45]([C:46]3[CH:47]=[CH:48][C:49]([Cl:52])=[CH:50][CH:51]=3)[CH2:44][NH:43][CH2:42]2)[CH2:39][CH3:40])=[CH:32][CH:31]=1

참가 물질

3

반응물 2

HCID 53247231rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl esterHCID 67238593HCID 67238593, 화합물

생성물 1

HCID 58312626HCID 58312626, 화합물

실험 절차

In analogy to the procedure described for rac-(3S,4R)-[3-Amino-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone (example 1, f) the Boc protecting group was removed. The liberated amine was reacted to the respective carbamate in analogy to the procedure described for the synthesis of rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl ester (example 1, h). The benzyl protecting group was removed in analogy to the procedure described for rac-(3S,4R)-[4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (example 1, d) to yield the title compound as amorphous crude brown foam. MS m/e: 363.3 [M+H]+.

후처리

  1. customwas removed
  2. customThe liberated amine was reacted to the respective carbamate in analogy to the procedure
  3. customThe benzyl protecting group was removed in analogy to the procedure

출처 및 근거

ORD 기록
ord-83463d2b3d5f4d74a69cb085676ab295
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346786B2

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