Sodium Hydroxide → 4-Ethyl-1-(5-(2-(3-ethylureido)-7-propionylbenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylic acid

HRID 712342Notes

Reaction equation

HRID 712342 reaction equation
[CH2:1]([C:3]1([C:34]([O:36]CC)=[O:35])[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:16]=[C:17]([C:30](=[O:33])[CH2:31][CH3:32])[C:18]4[S:22][C:21]([NH:23][C:24]([NH:26][CH2:27][CH3:28])=[O:25])=[N:20][C:19]=4[CH:29]=3)=[CH:11][N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[OH-].[Na+]>CCO>[CH2:1]([C:3]1([C:34]([OH:36])=[O:35])[CH2:4][CH2:5][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:16]=[C:17]([C:30](=[O:33])[CH2:31][CH3:32])[C:18]4[S:22][C:21]([NH:23][C:24]([NH:26][CH2:27][CH3:28])=[O:25])=[N:20][C:19]=4[CH:29]=3)=[CH:11][N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86664049Ethyl 4-ethyl-1-(5-(2-(3-ethylureido)-7-propionylbenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate

Product 1

HCID 872225034-Ethyl-1-(5-(2-(3-ethylureido)-7-propionylbenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylic acidYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 4-ethyl-1-(5-(2-(3-ethylureido)-7-propionylbenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate (0.025 g, 0.046 mmol) in EtOH (5 mL) was added an aqueous solution (1 mL) of NaOH (0.0092 g, 0.232 mmol) and the mixture stirred overnight at 80° C. After reaction completion (by TLC), the EtOH was evaporated under reduced pressure, water (10 mL) was added to the residue and extracted with EtOAc (3×25 mL) and the organic layers discarded. The aqueous layer was acidified to pH 4-5 with 1N HCl, extracted with EtOAc (3×25 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4, filtered then concentrated under reduced pressure. The residue was purified by preparative TLC (5% MeOH in DCM) to obtain Compound 207 as white solid (0.007 g, 30%). 1H NMR (DMSO-d6): δ 10.82 (br s, 1H), 8.86 (s, 2H), 8.23 (s, 1H), 8.14 (s, 1H), 6.95 (br s, 1H), 4.46 (m, 2H), 3.36 (m, 2H), 3.13-3.24 (m, 4H), 2.08 (m, 2H), 1.51-1.53 (m, 2H), 1.32 (m, 2H), 1.16 (t, J=7.2 Hz, 3H), 1.10 (t, J=7.2 Hz, 3H) and 0.81 (t, J=7.2 Hz, 3H). MS: 511.24 [M+H]+.

Workup

  1. customAfter reaction completion (by TLC)
  2. customthe EtOH was evaporated under reduced pressure, water (10 mL)
  3. additionwas added to the residue
  4. extractionextracted with EtOAc (3×25 mL)
  5. extractionextracted with EtOAc (3×25 mL)
  6. washthe combined organic layers washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationthen concentrated under reduced pressure
  10. customThe residue was purified by preparative TLC (5% MeOH in DCM)

Sources & evidence

ORD record
ord-63a5ff0612944354aa9013015494a40e
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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