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

HRID 63684

반응식

HRID 63684 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].[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21][C:22]([CH3:24])=O.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][C@H:30]1[C:35]([OH:37])=[O:36].S1C=CN=C1C(N)=N.C(OC)(=O)CC(C)=O.FC1(F)CN[C@H](C(O)=O)C1>>[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:22]([CH2:24][N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@H:30]2[C:35]([OH:37])=[O:36])=[C:21]1[C:20]([O:26][CH2:27][CH3:28])=[O:25]

참가 물질

8

반응물 7

HCID 7757Methyl acetoacetateHCID 8868Ethyl AcetoacetateHCID 1501894(S)-morpholine-3-carboxylic acidHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 108879112-ThiazolecarboximidamideHCID 152161024,4-DifluoroprolineHCID 836773875-Methyl-oxazole-4-carboxamidine

생성물 1

HCID 73330831(S)-4-[(R)-6-(2-Bromo-4-fluoro-phenyl)-5-ethoxycarbonyl-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 1 with Procedure A shown in Scheme 4 by using 2-bromo-4-fluorobenzaldehyde, 5-methyl-oxazole-4-carboxamidine (Compound AB), ethyl acetoacetate and (S)-morpholine-3-carboxylic acid instead of 2-chloro-4-fluorobenzaldehyde, thiazole-2-carboxamidine, methyl acetoacetate and (S)-4,4-difluoro-pyrrolidine-2-carboxylic acid. The stereochemistry of Example 69 was determined by comparing its 1H NMR data and HPLC retention time with Example 2.

출처 및 근거

ORD 기록
ord-ddeb826efca34604a1af67507d528343
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447086B2

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