Diisopropylethylamine → (S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid (5-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-pyrazol-3-yl}-2-methyl-phenyl)-amide

HRID 1697881노트

반응식

HRID 1697881 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]=[C:9]2[C:15]([OH:17])=O)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:51]([Si:55]([CH3:74])([CH3:73])[O:56][CH2:57][CH2:58][N:59]1[C:63]([CH3:64])=[CH:62][C:61]([C:65]2[CH:66]=[CH:67][C:68]([CH3:72])=[C:69]([NH2:71])[CH:70]=2)=[N:60]1)([CH3:54])([CH3:53])[CH3:52]>CN1C(=O)CCC1.O>[C:51]([Si:55]([CH3:74])([CH3:73])[O:56][CH2:57][CH2:58][N:59]1[C:63]([CH3:64])=[CH:62][C:61]([C:65]2[CH:66]=[CH:67][C:68]([CH3:72])=[C:69]([NH:71][C:15]([C:9]3[C@H:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:13][C:12](=[O:14])[NH:11][CH:10]=3)=[O:17])[CH:70]=2)=[N:60]1)([CH3:53])([CH3:52])[CH3:54]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45378709HCID 45378709, 화합물HCID 66955104HCID 66955104, 화합물

생성물 1

HCID 67277422(S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid (5-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-pyrazol-3-yl}-2-methyl-phenyl)-amide수율 40.6%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매2회

실험 절차

A solution of (S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid (138 mg), N,N-Diisopropylethylamine (155 mg) and HATU (152 mg) in NMP (1 ml) was stirred at room temperature for 10 minutes. A solution of 5-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-pyrazol-3-yl}-2-methyl-phenylamine (94 mg) in NMP (1 ml) was added, and the reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by “flash chromatography” (0 to 5% MeOH in CH2Cl2) to give 62.2 mg of (S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid (5-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-pyrazol-3-yl}-2-methyl-phenyl)-amide as an amorphous solid.

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by “flash chromatography” (0 to 5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-aef0caf7e06b4e2697446b69a7d7b519
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163929B2

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