Cesium carbonate → HCID 136629526, compound

HRID 869121Notes

Reaction equation

HRID 869121 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[O:16][CH3:17])=[O:8])=[C:5]([NH2:18])[NH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:25](OC)(=[O:28])[C:26]#[CH:27]>CCO>[NH2:18][C:5]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[O:16][CH3:17])=[O:8])=[C:2]2[NH:1][C:25](=[O:28])[CH:26]=[CH:27][N:3]2[N:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13536Methyl propiolateHCID 90410181HCID 90410181, compound

Product 1

HCID 136629526HCID 136629526, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3,5-diamino-N-(4-methoxy-3-pyridyl)-1H-pyrazole-4-carboxamide 9 (300 mg, 1.209 mmol) and Cs2CO3 (591 mg, 1.814 mmol) in EtOH (5 mL) was added methyl prop-2-ynoate (203.3 mg, 215.1 μL, 2.418 mmol), dropwise, over 15 minutes and the reaction mixture was stirred overnight at room temperature. The mixture was filtered and product purified by preparative HPLC. Solvents were evaporated in vacuum to afford the product as a yellow solid (yield 27%). LC-MS (M+H)+=301.1; 1H NMR (500 MHz, DMSO-d6) δ 10.18 (s, 1H), 9.58 (s, 1H), 8.71 (d, 1H), 8.58 (d, 1H), 7.68 (d, 1H), 6.45 (d, 1H), 6.38-6.28 (m, 2H), 4.25 (s, 3H);

Workup

  1. filtrationThe mixture was filtered
  2. customproduct purified by preparative HPLC
  3. customSolvents were evaporated in vacuum

Sources & evidence

ORD record
ord-319b5a52d34d42cbbf55ae6d90ca5287
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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