Water → HCID 56953308, compound

HRID 712299Notes

Reaction equation

HRID 712299 reaction equation
[CH2:1]([NH:3][C:4](=[O:42])[NH:5][C:6]1[S:7][C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:13][C:12]([C:21]3[CH:22]=[N:23][C:24]([N:27]4[CH2:32][CH2:31][C:30]([C:38]([F:41])([F:40])[F:39])([C:33]([O:35]CC)=[O:34])[CH2:29][CH2:28]4)=[N:25][CH:26]=3)=[CH:11][C:9]=2[N:10]=1)[CH3:2].CC(C)([O-])C.[K+].O>CS(C)=O>[CH2:1]([NH:3][C:4]([NH:5][C:6]1[S:7][C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:13][C:12]([C:21]3[CH:22]=[N:23][C:24]([N:27]4[CH2:28][CH2:29][C:30]([C:38]([F:41])([F:40])[F:39])([C:33]([OH:35])=[O:34])[CH2:31][CH2:32]4)=[N:25][CH:26]=3)=[CH:11][C:9]=2[N:10]=1)=[O:42])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86664014HCID 86664014, compound

Product 1

HCID 56953308HCID 56953308, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an ice-cold solution of ethyl 1-(5-(2-(3-ethylureido)-7-(pyridin-2-yl)benzothiazol-5-yl)pyrimidin-2-yl)-4-(trifluoromethyl)piperidine-4-carboxylate (0.05 g, 0.08 mmol) in DMSO (2.0 mL) was added potassium tert-butoxide (0.046 g, 0.41 mmol) and the mixture stirred at rt for 2 h. After completion of reaction (by TLC), water (10 mL) was added followed by extraction with EtOAc (2×50 mL) and the organic layer discarded. The pH of the aqueous layer was adjusted up to 4-5 then extracted with hot EtOAc (3×75 mL) and the combined organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with ether to afford Compound 142 as off-white solid (0.04 g, 84% yield). 1H NMR (DMSO-d6): δ 1.09 (t, J=7.20 Hz, 3H), 1.65 (m, 2H), 2.31 (m, 2H), 3.01 (m, 2H), 3.20 (q, J=7.20 Hz, 2H), 4.75 (m, 2H), 6.87 (br s, 1H, D2O exchangeable), 7.43 (m, 1H), 7.99 (m, 2H), 8.23 (s, 1H), 8.48 (d, J=7.20 Hz, 1H), 8.80 (d, J=3.60 Hz, 1H), 8.92 (s, 2H), 10.57 (br s, 1H, D2O exchangeable) and 14.06 (br s, 1H, D2O exchangeable). MS: 572.10 [M+H]+.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc (2×50 mL)
  3. extractionthen extracted with hot EtOAc (3×75 mL)
  4. dry with materialthe combined organic layer dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue thus obtained
  8. customwas triturated with ether

Sources & evidence

ORD record
ord-cb76c070732b4516b36b0e8874dd5018
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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