Water → HCID 86664013, compound

HRID 712297Notes

Reaction equation

HRID 712297 reaction equation
[CH2:1]([C:4]1([C:37]([O:39]CC)=[O:38])[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]([C:31]4[CH:36]=[N:35][CH:34]=[CH:33][N:32]=4)[C:19]4[S:23][C:22]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[N:21][C:20]=4[CH:30]=3)=[CH:12][N:11]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].CC(C)([O-])C.[K+].O>CS(C)=O>[CH2:1]([C:4]1([C:37]([OH:39])=[O:38])[CH2:5][CH2:6][N:7]([C:10]2[N:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]([C:31]4[CH:36]=[N:35][CH:34]=[CH:33][N:32]=4)[C:19]4[S:23][C:22]([NH:24][C:25](=[O:26])[NH:27][CH2:28][CH3:29])=[N:21][C:20]=4[CH:30]=3)=[CH:12][N:11]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86664010HCID 86664010, compound

Product 1

HCID 86664013HCID 86664013, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an ice-cold solution of ethyl 4-allyl-1-(5-(2-(3-ethylureido)-7-(pyrazin-2-yl)benzothiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate (0.26 g, 0.45 mmol) in DMSO (2.0 mL) was added potassium tert-butoxide (0.25 g, 2.25 mmol). The resulting mixture was 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). The organic layer was discarded and the pH of the aqueous layer was adjusted up to 4-5, then extracted with hot EtOAc (3×100 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 139 as a beige solid (0.13 g, 53% yield). 1H NMR (DMSO-d6): δ 1.09 (t, J=7.20 Hz, 3H), 1.44 (m, 2H), 2.05 (m, 2H), 2.29 (m, 2H), 3.17-3.22 (m, 4H), 4.43 (m, 2H), 5.07 (m, 2H), 5.71 (m, 1H), 6.90 (br s, 1H), 8.03 (s, 1H), 8.40 (s, 1H), 8.69 (d, J=2.80 Hz, 1H), 8.87 (d, J=2.0 Hz, 1H), 8.94 (s, 2H), 9.77 (s, 1H), 10.71 (br s, 1H) and 12.69 (br s, 1H). MS: 545.26 [M+H]+.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc (2×50 mL)
  3. extractionextracted with hot EtOAc (3×100 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-c1d87fdd4ee546af9ca8510c656912c5
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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