Water → HCID 50943778, compound

HRID 1484953Notes

Reaction equation

HRID 1484953 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[C:8]([NH:22][C:23]2[CH:27]=[C:26]([CH:28]3[CH2:30][CH2:29]3)[NH:25][N:24]=2)=[N:9][C:10]([C:13]2[S:14][C:15]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:16][CH:17]=2)=[N:11][CH:12]=1)(=O)C.[OH-].[Na+].O>CO>[CH:28]1([C:26]2[NH:25][N:24]=[C:23]([NH:22][C:8]3[C:7]([CH2:6][CH2:5][OH:4])=[CH:12][N:11]=[C:10]([C:13]4[S:14][C:15]([S:18]([NH2:19])(=[O:21])=[O:20])=[CH:16][CH:17]=4)[N:9]=3)[CH:27]=2)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 50943863HCID 50943863, compound2×

Product 1

HCID 50943778HCID 50943778, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-(5-sulfamoylthiophen-2-yl)pyrimidin-5-yl)ethyl acetate (Compound 313) (200 mg, 0.45 mmol, 1.0 equiv.) and NaOH.aq (2 mL) in MeOH (5 mL) was stirred for 1 h at rt. Water was added and the mixture was extracted with EtOAc. The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated to yield 5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(2-hydroxyethyl)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 239) (120 mg, 66%). LC-MS (m/z)=407.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.77-0.81 (m, 2H), 1.01-1.06 (m, 2H), 1.97-2.01 (m, 1H), 2.89 (t, J=5.6 Hz, 2H), 3.69 (d, J=5.6 Hz, 2H), 6.47 (s, 1H), 7.69 (d, J=4.0 Hz, 1H), 7.98 (s, 2H), 8.23 (s, 1H), 8.34 (d, J=3.2 Hz, 1H), 10.67 (s, 1H)

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic phases were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0d0e4bae7e4e42e9b6e8cc7e40f1d598
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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