Tetramethyltin → 1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-{(s)-2-[(5-methyl-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl}-methanone

HRID 18109

반응식

HRID 18109 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([C:17]2[N:18]=[C:19]([CH3:29])[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:16])=[N:6][CH:7]=1.[Cl-].[Li+].[CH3:32][Sn](C)(C)C>CN(C)C=O>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]2[S:20][C:19]([CH3:29])=[N:18][C:17]=2[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[CH2:9][NH:8][C:5]2[N:4]=[CH:3][C:2]([CH3:32])=[CH:7][N:6]=2)=[O:16])=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 11661TetramethyltinHCID 433294Lithium ChlorideHCID 670897411-{(S)-2-[(5-Bromo-pyrimidin-2-ylamino)methyl]-pyrrolidin-1-yl}-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone

생성물 1

HCID 670901811-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-{(s)-2-[(5-methyl-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl}-methanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To the compound of Example 194 (0.36 g) in dimethylformamide was added lithium chloride (0.096 g), tetramethyl tin (0.126 ml) and dichlorobis(triphenylphosphine) palladium (0) (0.035 g) and the resulting mixture heated at 100° C. under argon for 18 h. The reaction was then evaporated, diluted with dichloromethane, filtered and the filtrate washed with water, dried and evaporated. Chromatography of the residue on silica gel, eluting with methanol-dichloromethane mixtures, afforded the title product (0.2 g) as a yellow amorphous solid. Mass Spectrum (API+): Found 412 (MH+). C21H22FN5OS requires 411.

후처리

  1. customThe reaction was then evaporated
  2. additiondiluted with dichloromethane
  3. filtrationfiltered
  4. washthe filtrate washed with water
  5. customdried
  6. customevaporated
  7. washChromatography of the residue on silica gel, eluting with methanol-dichloromethane mixtures

출처 및 근거

ORD 기록
ord-4893d11d1a2144649e424973006797cd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741329B2

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