Water → HCID 72724620, compound

HRID 712254Notes

Reaction equation

HRID 712254 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[CH2:33][CH2:32][C:31]([CH3:39])([C:34]([O:36]CC)=[O:35])[CH2:30][CH2:29]4)=[N:26][CH:27]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].CC(C)([O-])C.[K+].O>CS(C)=O>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([C:22]3[CH:27]=[N:26][C:25]([N:28]4[CH2:29][CH2:30][C:31]([CH3:39])([C:34]([OH:36])=[O:35])[CH2:32][CH2:33]4)=[N:24][CH:23]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86663969HCID 86663969, compound

Product 1

HCID 72724620HCID 72724620, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an ice-cold solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (0.18 g, 0.33 mmol) in DMSO (2 mL) was added potassium tert-butoxide (0.184 g, 1.65 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). 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). The combined organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with ether to afford the desired product as off-white solid (0.11 g, 65% yield). 1H NMR (DMSO-d6): δ 1.10 (t, J=7.20 Hz, 3H), 1.19 (s, 3H), 1.40 (m, 2H), 2.04 (m, 2H), 3.22 (q, J=7.20, 2H), 3.39 (m, 2H), 4.30 (m, 2H), 6.87 (br s, 1H, D2O exchangeable), 7.44 (m, 1H), 7.92 (s, 1H), 7.99 (m, 1H), 8.18 (s, 1H), 8.42 (d, J=8.0 Hz, 1H), 8.78 (d, (J=4.40 Hz, 1H), 8.85 (s, 2H), 10.54 (br s, 1H, D2O exchangeable) and 12.45 (br s, 1H, D2O exchangeable). MS: 518.27 [M+H]+.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc (2×50 mL)
  3. extractionthen extracted with hot EtOAc (3×100 mL)
  4. dry with materialThe combined organic layer was 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-b5a89b74fb114aafab67b3d908c4f4c0
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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