Potassium Hydroxide → Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

HRID 712311Notes

Reaction equation

HRID 712311 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]#[C:17][Si](C)(C)C)=[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][CH2:37][CH3:38])=[O:35])[CH2:30][CH2:29]4)=[N:26][CH:27]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[OH-].[K+]>CCO>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]#[CH:17])=[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]([O:36][CH2:37][CH3:38])=[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

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86664024Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(2-trimethylsilylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Product 1

HCID 86663977Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylateYield 83.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cold solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(2-trimethylsilylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (1.1 g, 1.94 mmol) in EtOH (40 mL) was added powdered KOH (0.24 g, 4.21 mmol) and the mixture stirred at rt for 4 h. After completion of reaction (by TLC), the solvent was evaporated under reduced pressure, water added and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine and water then dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure to obtain the product as a pale yellow solid (0.8 g, 83% yield). 1H NMR (DMSO-d6): δ 1.11 (t, J=7.20 Hz, 3H), 1.21 (m, 6H), 1.42 (m, 2H), 2.04 (m, 2H), 3.20 (m, 2H), 3.33 (q, J=7.20, 2H), 4.13 (q, J=6.80 Hz, 2H), 4.25 (m, 2H), 4.67 (s, 1H), 6.80 (br s, 1H), 7.61 (s, 1H), 7.94 (s, 1H); 8.78 (s, 2H) and 10.86 (br s, 1H). MS: 493.12 [M+H]+.

Workup

  1. customAfter completion of reaction (by TLC)
  2. customthe solvent was evaporated under reduced pressure, water
  3. additionadded
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic layer was washed with brine and water
  6. dry with materialthen dried over anhydrous Na2SO4
  7. customSolvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9037c72c665048ea847e609e8cafdcb4
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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