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 40849

Reaction equation

HRID 40849 reaction equation
[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]

Participants

4

Reactant 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

Product 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-carbonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ddc6ea2db9dc41b084e57c68cf3315dd
Source dataset
uspto-grants-2013_09
Patent number
US08530489B2

Linked notes

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