Potassium Carbonate → HCID 58169453, compound

HRID 1484962Notes

Reaction equation

HRID 1484962 reaction equation
C([N:4]1[C:8]([CH:9]2[CH2:11][CH2:10]2)=[CH:7][C:6]([NH:12][C:13]2[C:18]([C:19]#[CH:20])=[CH:17][N:16]=[C:15]([C:21]3[S:25][C:24]([S:26]([NH:29][C:30](=[O:32])[CH3:31])(=[O:28])=[O:27])=[CH:23][CH:22]=3)[N:14]=2)=[N:5]1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CCO>[CH:9]1([C:8]2[NH:4][N:5]=[C:6]([NH:12][C:13]3[C:18]([C:19]#[CH:20])=[CH:17][N:16]=[C:15]([C:21]4[S:25][C:24]([S:26]([NH:29][C:30](=[O:32])[CH3:31])(=[O:27])=[O:28])=[CH:23][CH:22]=4)[N:14]=3)[CH:7]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58169545HCID 58169545, compound

Product 1

HCID 58169453HCID 58169453, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of crude N-(5-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-ylsulfonyl)acetamide and K2CO3 (43 mg, 0.31 mmol, 2.4 eq) in EtOH (10 mL) was stirred at room temperature for 1 h. The reaction mixture was filtered, the filtrate was concentrated. The residue was diluted with EtOAc and washed with water, brine, dried (Na2SO4), and filtered. The filtrate was concentrated and crystallized with ether to yield N-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-ylsulfonyl)acetamide (Compound 192) (65 mg, 84%). LC-MS (m/z)=429 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 0.74-0.77 (m, 2H), 0.97-0.99 (m, 2H), 1.71 (s, 3H), 1.92-1.99 (m, 1H), 4.87 (s, 1H), 6.49 (s, 1H), 7.41 (d, J=4.0 Hz, 1H), 7.66 (d, J=3.6 Hz, 1H), 8.47 (s, 1H), 8.57 (bs, 1H), 12.31 (bs, 1H)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was diluted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customcrystallized with ether

Sources & evidence

ORD record
ord-5841390d82fc4595817ccb8972e1bc88
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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