Methanol → HCID 86664035, compound

HRID 712320Notes

Reaction equation

HRID 712320 reaction equation
C([O:3][C:4]([C:6]1([CH2:35][CH3:36])[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([CH:33]=[O:34])[C:21]4[S:25][C:24]([NH:26][C:27](=[O:31])[NH:28][CH2:29][CH3:30])=[N:23][C:22]=4[CH:32]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.CO.[OH-].[K+]>C1COCC1.O>[CH2:35]([C:6]1([C:4]([OH:5])=[O:3])[CH2:11][CH2:10][N:9]([C:12]2[N:13]=[CH:14][C:15]([C:18]3[CH:19]=[C:20]([CH:33]=[O:34])[C:21]4[S:25][C:24]([NH:26][C:27](=[O:31])[NH:28][CH2:29][CH3:30])=[N:23][C:22]=4[CH:32]=3)=[CH:16][N:17]=2)[CH2:8][CH2:7]1)[CH3:36]

Participants

6

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 86664033HCID 86664033, compound

Product 1

HCID 86664035HCID 86664035, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl-4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate (1.75 g, 3.43 mmol) was dissolved in THF (60 mL) and MeOH (125 mL) and an aqueous solution of KOH (125 mL; 1 mol/L) was introduced and refluxed overnight. After this period the mixture was diluted with water (150 mL), washed with Et2O/EtOAc (1:1, 100 mL) and the residual aqueous acidified to pH 1 (3M HCl) and back extracted with EtOAc (3×100 mL). The organic fractions were combined, dried (MgSO4) and concentrated in vacuo affording 1.05 g (64% yield) of the product as a light yellow solid after flash column chromatography on silica gel (0-10% DCM/MeOH). 1HNMR (CDCl3): δ 10.16 (s, 1H), 8.56 (d, J=20.7 Hz, 2H), 7.95 (d, J=1.5 Hz, 1H), 7.81 (d, J=1.6 Hz, 1H), 4.51 (d, J=13.9 Hz, 2H), 3.39-3.32 (m, 2H), 3.26-3.15 (m, 2H), 2.20 (d, J=13.4 Hz, 2H), 1.59 (q, J=7.5 Hz, 2H), 1.48-1.34 (m, 2H), 1.21 (t, J=7.2 Hz, 3H), 0.87 (t, J=7.5 Hz, 3H). MS: 483.1 [M+H]+.

Workup

  1. temperaturerefluxed overnight
  2. washwashed with Et2O/EtOAc (1:1, 100 mL)
  3. extractionback extracted with EtOAc (3×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6d6f1794cec41eaba69c2a072598614
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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