Water → HCID 178465314, compound

HRID 712359Notes

Reaction equation

HRID 712359 reaction equation
[CH2:1]([C:3]1([C:36]([O:38]CC)=[O:37])[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:29]=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)[C:18]4[NH:19][C:20]([NH:22][C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[N:21][C:17]=4[CH:16]=3)=[CH:11][N:10]=2)[CH2:5][CH2:4]1)[CH3:2].CC(C)([O-])C.[K+].O>CS(C)=O>[CH2:1]([C:3]1([C:36]([OH:38])=[O:37])[CH2:8][CH2:7][N:6]([C:9]2[N:10]=[CH:11][C:12]([C:15]3[CH:29]=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)[C:18]4[NH:19][C:20]([NH:22][C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[N:21][C:17]=4[CH:16]=3)=[CH:13][N:14]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 178465315HCID 178465315, compound

Product 1

HCID 178465314HCID 178465314, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an ice-cold solution of ethyl 4-ethyl-1-(5-(2-(3-ethylureido)-7-(pyridin-2-yl)-1H-benzo[d]imidazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate (0.20 g, 0.37 mmol) in DMSO (3.0 mL) was added potassium tert-butoxide (0.2.06 g, 1.84 mmol) and the mixture stirred at rt for 16 h. After completion of reaction (by TLC), water (10 mL) was added followed by extraction with EtOAc (3×25 mL) and the organic layer discarded. The pH of the aqueous layer was adjusted up to 4-5, extracted with EtOAc (3×25 mL) and the combined organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with n-pentane to afford Compound 229 as yellow solid (0.10 g, 53%). 1H NMR (DMSO-d6+D2O): δ 8.78 (m, 3H), 8.38 (m, 1H), 7.95-8.0 (m, 2H), 7.69 (s, 1H), 7.39 (br s, 1H), 4.44 (m, 2H), 3.22 (m, 2H), 3.13 (m, 2H), 2.06 (m, 2H), 1.51 (m, 2H), 1.34 (m, 2H), 1.11 (t, J=7.20 Hz, 3H) and 0.80 (t, J=7.20 Hz, 3H). LCMS: 515.19 [M+H]+

Workup

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc (3×25 mL)
  3. extractionextracted with EtOAc (3×25 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 n-pentane

Sources & evidence

ORD record
ord-145b9fe22bfd4ca58db6b4c93b0422b8
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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