Water → HCID 86664027, compound

HRID 712315Notes

Reaction equation

HRID 712315 reaction equation
[CH2:1]([NH:3][C:4](=[O:39])[NH:5][C:6]1[S:7][C:8]2[C:9]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[N:10][C:11]([C:15]3[CH:16]=[N:17][C:18]([N:21]4[CH2:26][CH2:25][C:24]([CH3:32])([C:27]([O:29]CC)=[O:28])[CH2:23][CH2:22]4)=[N:19][CH:20]=3)=[CH:12][C:13]=2[N:14]=1)[CH3:2].CC(C)([O-])C.[K+].O>CS(C)=O>[CH2:1]([NH:3][C:4](=[O:39])[NH:5][C:6]1[S:7][C:8]2[C:9]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[N:10][C:11]([C:15]3[CH:16]=[N:17][C:18]([N:21]4[CH2:26][CH2:25][C:24]([CH3:32])([C:27]([OH:29])=[O:28])[CH2:23][CH2:22]4)=[N:19][CH:20]=3)=[CH:12][C:13]=2[N:14]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86664028HCID 86664028, compound

Product 1

HCID 86664027HCID 86664027, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of ethyl 1-(5-(2-(3-ethylureido)-4-(pyridin-2-yl)thiazolo[5,4-c]pyridin-6-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate (0.050 g, 0.091 mmol) in DMSO (2.0 mL) at rt was added potassium tert-butoxide (0.052 g, 0.45 mmol) and the mixture stirred at rt for 15-20 min. After completion of reaction (by TLC), water (25 mL) was added, followed by extraction with EtOAc (3×50 mL) and the organic layer was discarded. The pH of the aqueous layer was adjusted up to 4-5, extracted with hot EtOAc (3×50 mL) and the combined organic layer washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with ether to afford Compound 162 (0.030 g, 64%). 1H NMR (DMSO-d6): δ 1.10 (t, J=7.20 Hz, 3H), 1.20 (s, 3H), 1.44 (m, 2H), 2.04 (m, 2H), 3.22 (m, 2H), 3.37 (m, 2H), 4.35 (m, 2H), 6.86 (br s, 1H), 7.53 (m, 1H), 8.05 (m, 1H), 8.16 (s, 1H), 8.80 (d, J=8.40 Hz, 1H), 8.84 (d, J=4.40 Hz, 1H), 9.26 (s, 2H), 10.93 (br s, 1H) and 12.45 (br s, 1H). MS: 519.28 [M+H]+.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc (3×50 mL)
  3. extractionextracted with hot EtOAc (3×50 mL)
  4. washthe combined organic layer washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue thus obtained
  9. customwas triturated with ether

Sources & evidence

ORD record
ord-2979152f81d540b394a152492a23174f
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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