Water → HCID 57471654, compound

HRID 40858Notes

Reaction equation

HRID 40858 reaction equation
[C:1]([C:3]1[C:4]([C:21]2[C:29]3[C:24](=[N:25][CH:26]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:28]=3)[N:23](S(C3C=CC(C)=CC=3)(=O)=O)[CH:22]=2)=[N:5][C:6]([NH:9][C:10]([CH3:20])([CH3:19])[C:11]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[O:12])=[N:7][CH:8]=1)#[N:2].O.O[Li].O>C1COCC1>[C:1]([C:3]1[C:4]([C:21]2[C:29]3[C:24](=[N:25][CH:26]=[C:27]([C:30]([F:31])([F:33])[F:32])[CH:28]=3)[NH:23][CH:22]=2)=[N:5][C:6]([NH:9][C:10]([CH3:20])([CH3:19])[C:11]([NH:13][CH2:14][C:15]([F:18])([F:16])[F:17])=[O:12])=[N:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59414605HCID 59414605, compound

Product 1

HCID 57471654HCID 57471654, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(5-cyano-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-ylamino)-2-methyl-N-(2,2,2-trifluoroethyl)propanamide (29 mg, 0.046 mmol, 1.0 Eq.) was dissolved in THF (4 mL) and water (1 mL) and treated with LiOH.H2O (10 mg, 0.23 mmol, 15 eq) and allowed to stir at room temperature overnight. The reaction mixture was concentrated and the residue partitioned between EtOAc and water. The organic phase was washed with saturated aqueous NaHCO3 followed by brine, dried over MgSO4, filtered and the solvent evaporated. The residue was purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petroleum Ether) to give the title compound as a white solid (13 mg, 60%). MS (ES+) m/e=472. 1H NMR (DMSO) 1.53 (6H, s), 1.58 (6H, s), 3.65-3.69 (2H, m), 3.75-3.79 (2H, m), 8.26-8.34 (2H, m), 8.45 (1H, s), 8.65-8.78 (6H, m), 8.96 (1H, s), 9.29 (1H, s), 13.05 (2H, brs) [1:1 Mixture of rotamers]

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between EtOAc and water
  3. washThe organic phase was washed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue was purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petroleum Ether)

Sources & evidence

ORD record
ord-b10adb7b41234f1faf4f018ba07afc18
Source dataset
uspto-grants-2013_09
Patent number
US08530489B2

Reaction notes

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