Lithium Hydroxide → 2-((R)-1-(1-(2-hydroxyacetyl)piperidin-4-yl)ethylamino)-4-(5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 1853475

반응식

HRID 1853475 반응식
[OH-].[Li+].[OH:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C@H:13]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[C:30]4[C:25](=[N:26][CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=4)[N:24](S(C4C=CC(C)=CC=4)(=O)=O)[CH:23]=3)[C:19]([C:45]#[N:46])=[CH:18][N:17]=2)[CH3:14])[CH2:9][CH2:8]1)=[O:6]>O1CCCC1>[OH:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C@H:13]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[C:30]4[C:25](=[N:26][CH:27]=[C:28]([C:31]([F:33])([F:34])[F:32])[CH:29]=4)[NH:24][CH:23]=3)[C:19]([C:45]#[N:46])=[CH:18][N:17]=2)[CH3:14])[CH2:9][CH2:8]1)=[O:6]

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 594146092-((R)-1-(1-(2-hydroxyacetyl)piperidin-4-yl)ethylamino)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

생성물 1

HCID 574658362-((R)-1-(1-(2-hydroxyacetyl)piperidin-4-yl)ethylamino)-4-(5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1M solution of lithium hydroxide (382.5 μl, 0.38 mmol) was added to a solution of 2-((R)-1-(1-(2-hydroxyacetyl)piperidin-4-yl)ethylamino)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile (80 mg, 0.128 mmol) in tetrahydrofuran (2 mL). The reaction mixture was stirred at room temperature for 1 hour. The crude mixture was concentrated to dryness and redissolved in ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography (ISCO Companion|) to afford the title compound as a white solid (30 mg, 50% yield).

후처리

  1. concentrationThe crude mixture was concentrated to dryness
  2. dissolutionredissolved in ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by flash column chromatography (ISCO Companion|)

출처 및 근거

ORD 기록
ord-b352a174b95e4607a9fffc3feec1ab00
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962642B2

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