Potassium Carbonate → HCID 50943693, compound

HRID 1484930Notes

Reaction equation

HRID 1484930 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[S:11][C:12]([C:15]2[N:20]=[C:19]([NH:21][C:22]3[CH:26]=[C:25]([CH:27]4[CH2:29][CH2:28]4)[N:24](C(=O)C)[N:23]=3)[C:18]([C:33]#[C:34][Si](C)(C)C)=[CH:17][N:16]=2)=[CH:13][CH:14]=1)=[O:9])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CCO>[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[S:11][C:12]([C:15]2[N:20]=[C:19]([NH:21][C:22]3[CH:26]=[C:25]([CH:27]4[CH2:28][CH2:29]4)[NH:24][N:23]=3)[C:18]([C:33]#[CH:34])=[CH:17][N:16]=2)=[CH:13][CH:14]=1)=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58169222HCID 58169222, compound

Product 1

HCID 50943693HCID 50943693, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of N-(2-acetamidoethyl)-5-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-5-((trimethylsilyl)ethynyl)pyrimidin-2-yl)thiophene-2-carboxamide (96.1 mg, 0.17 mmol, 1.0 eq) and K2CO3 (70.4 mg, 0.51 mmol, 3.0 eq) in EtOH (10 mL) was stirred at room temperature for 1 h. The reaction mixture was filtered. The filtrate was concentrated to 2 mL. The conc. liquid was extracted with EtOAc and washed with water, brine and dried (Na2SO4) and filtered. The filtrate was concentrated to generate N-(2-acetamidoethyl)-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophene-2-carboxamide (Compound 206) (53.2 mg, 72.1%) as pale yellow solid. LC-MS (m/z)=436.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.74-0.78 (m, 2H), 0.97-1.01 (m, 2H), 1.82 (s, 3H), 1.93-1.99 (m, 1H), 3.20-3.23 (m, 2H), 3.27-3.30 (m, 2H), 4.87 (m, 1H), 6.49 (m, 1H), 7.76 (d, J=4.4 Hz, 1H), 7.84 (d, J=4.0 Hz, 1H), 8.01 (t, J=5.2 Hz, 1H), 8.50 (s, 1H), 8.70 (t, J=5.2 Hz, 1H), 8.76 (s, 1H)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated to 2 mL
  3. extractionThe conc. liquid was extracted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3d3be056e59348e9b4b00d33298d644b
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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