Potassium Carbonate → HCID 50943862, compound

HRID 1484938Notes

Reaction equation

HRID 1484938 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([CH:26]4[CH2:28][CH2:27]4)[NH:23][N:22]=3)[C:17]([CH2:29][CH2:30][CH2:31][OH:32])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.C([O-])([O-])=O.[K+].[K+]>C(O)(C(F)(F)F)=O.CO>[CH:26]1([C:24]2[NH:23][N:22]=[C:21]([NH:20][C:18]3[C:17]([CH2:29][CH2:30][CH2:31][OH:32])=[CH:16][N:15]=[C:14]([C:11]4[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=4)[N:19]=3)[CH:25]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58169377HCID 58169377, compound

Product 1

HCID 50943862HCID 50943862, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(3-hydroxypropyl)pyrimidin-2-yl)thiophene-2-sulfonamide (10 mg, 0.02 mmol) in TFA (1 mL) was heated to reflux for 0.5 h. The reaction was removed in vacuo, to which K2CO3 (43 mg, 0.31 mmol) in MeOH (5 mL) was added. After stirring at room temperature for 1 h the reaction mixture was filtered, the filtrate was concentrated and purified by HPLC-prepare to afford the desired compound 5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(3-hydroxy propyl)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 311) (6 mg, 66.7%, two step). LC-MS (m/z)=421 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ: 0.75-0.79 (m, 2H), 0.99-1.03 (m, 2H), 1.71 (q, J=6.4 Hz, 2H), 1.94-1.99 (m, 1H), 2.71 (t, J=6.4 Hz, 2H), 3.47 (t, J=6.4 Hz, 2H), 6.45 (s, 1H), 7.64 (d, J=4.0 Hz, 1H), 7.80 (s, 2H), 8.05 (d, J=3.2 Hz, 1H), 8.22 (s, 1H), 10.06 (bs, 1H).

Workup

  1. temperatureto reflux for 0.5 h
  2. additionwas added
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by HPLC-prepare

Sources & evidence

ORD record
ord-1759b9d09dc348a7bbc948e18b7dae2a
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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