Ethyl Acetoacetate → (S)-4-[(S)-6-(3,4-Difluoro-phenyl)-5-ethoxycarbonyl-2-(1-methyl-1H-imidazol-2-yl)-3,6-dihydro-pyrimidin-4-ylmethyl]-morpholine-3-carboxylic acid

HRID 63681

반응식

HRID 63681 반응식
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=O.[CH3:20][N:21]1[CH:25]=[CH:24][N:23]=[C:22]1[C:26]#[N:27].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][C@H:29]1[C:34]([OH:36])=[O:35].ClC1C=C(F)C=CC=1C=O.S1C=C[N:49]=C1C#N.FC1(F)CN[C@H](C(O)=O)C1>>[F:10][C:11]1[CH:12]=[C:13]([C@@H:14]2[N:49]=[C:26]([C:22]3[N:21]([CH3:20])[CH:25]=[CH:24][N:23]=3)[NH:27][C:3]([CH2:5][N:28]3[CH2:33][CH2:32][O:31][CH2:30][C@H:29]3[C:34]([OH:36])=[O:35])=[C:2]2[C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH:16]=[CH:17][C:18]=1[F:19]

참가 물질

8

반응물 7

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 5880883,4-DifluorobenzaldehydeHCID 1501894(S)-morpholine-3-carboxylic acidHCID 109534431-Methyl-1H-imidazole-2-carbonitrileHCID 151114801,3-Thiazole-2-carbonitrileHCID 152161024,4-Difluoroproline

생성물 1

HCID 73331546(S)-4-[(S)-6-(3,4-Difluoro-phenyl)-5-ethoxycarbonyl-2-(1-methyl-1H-imidazol-2-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 ethyl acetoacetate, 3,4-difluoro-benzaldehyde, 1-methyl-1H-imidazole-2-carbonitrile and (S)-morpholine-3-carboxylic acid instead of methyl acetoacetate, 2-chloro-4-fluoro-benzaldehyde, thiazole-2-carbonitrile and (S)-4,4-difluoro-pyrrolidine-2-carboxylic acid. The stereochemistry of Example 57 was determined by comparing its 1H NMR data and HPLC retention time with Example 2.

출처 및 근거

ORD 기록
ord-e7c720d81ea8400086bde779fdcdb706
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447086B2

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