(S)-morpholine-3-carboxylic acid → (S)-4-[(R)-6-(2-Bromo-4-fluoro-phenyl)-5-methoxycarbonyl-2-(5-methyl-oxazol-4-yl)-3,6-dihydro-pyrimidin-4-ylmethyl]-morpholine-3-carboxylic acid

HRID 63682

반응식

HRID 63682 반응식
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]1[O:16][CH:15]=[N:14][C:13]=1[C:17]([NH2:19])=[NH:18].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][C@H:21]1[C:26]([OH:28])=[O:27].S1C=CN=[C:30]1C(N)=N.F[C:38]1(F)CN[C@H:40]([C:43]([OH:45])=[O:44])[CH2:39]1>>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C@@H:4]1[N:19]=[C:17]([C:13]2[N:14]=[CH:15][O:16][C:12]=2[CH3:11])[NH:18][C:39]([CH2:38][N:20]2[CH2:25][CH2:24][O:23][CH2:22][C@H:21]2[C:26]([OH:28])=[O:27])=[C:40]1[C:43]([O:45][CH3:30])=[O:44]

참가 물질

6

반응물 5

HCID 1501894(S)-morpholine-3-carboxylic acidHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 108879112-ThiazolecarboximidamideHCID 152161024,4-DifluoroprolineHCID 836773875-Methyl-oxazole-4-carboxamidine

생성물 1

HCID 73330682(S)-4-[(R)-6-(2-Bromo-4-fluoro-phenyl)-5-methoxycarbonyl-2-(5-methyl-oxazol-4-yl)-3,6-dihydro-pyrimidin-4-ylmethyl]-morpholine-3-carboxylic acid

실험 절차

The title compound was prepared in analogy to Example 2 with Procedure A shown in Scheme 4 by using 2-bromo-4-fluorobenzaldehyde, 5-methyl-oxazole-4-carboxamidine (Compound AB) and (S)-morpholine-3-carboxylic acid instead of 2-chloro-4-fluorobenzaldehyde, thiazole-2-carboxamidine and (S)-4,4-difluoro-pyrrolidine-2-carboxylic acid. The stereochemistry of Example 65 was determined by comparing its 1H NMR data and HPLC retention time with Example 2.

출처 및 근거

ORD 기록
ord-78fd8d9d13bb43169e879aecd66398a0
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447086B2

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