Methyl iodide → HCID 68786970, compound

HRID 1519815Notes

Reaction equation

HRID 1519815 reaction equation
IC.[C:3]([O-])([O-])=O.[K+].[K+].[Cl:9][C:10]1[C:11]([C:29]2[N:33]=[CH:32][NH:31][N:30]=2)=[C:12]([NH:15][C:16](=[O:28])[CH2:17][N:18]2[C:23](=[O:24])[CH:22]=[CH:21][N:20]3[N:25]=[CH:26][CH:27]=[C:19]23)[S:13][CH:14]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:9][C:10]1[C:11]([C:29]2[N:33]=[CH:32][N:31]([CH3:3])[N:30]=2)=[C:12]([NH:15][C:16](=[O:28])[CH2:17][N:18]2[C:23](=[O:24])[CH:22]=[CH:21][N:20]3[N:25]=[CH:26][CH:27]=[C:19]23)[S:13][CH:14]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178521254HCID 178521254, compound

Product 1

HCID 68786970HCID 68786970, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodomethane (36 mg, 0.255 mmol) and K2CO3 (44 mg, 0.319 mmol) were added to a solution of N-(4-chloro-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(5-oxopyrazolo[1,5-a]pyrimidin-4(5H)-yl)acetamide (80 mg, 0.212 mmol) in DMF (1 mL). The reaction mixture was stirred at room temperature for 30 minutes and was subsequently diluted with ethyl acetate and washed with brine. The organic phase was dried (Na2SO4), filtered, concentrated under vacuum and purified by preparative HPLC to give N-(4-chloro-3-(1-methyl-1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(5-oxopyrazolo[1,5-a]pyrimidin-4(5H)-yl)acetamide. Retention time (min)=3.00, method [7], MS(ESI) 390.1 (M+H); 1H NMR (300 MHz, CD3Cl) δ 8.25 (d, J=8.2 Hz, 1H), 7.90 (s, 1H), 7.76 (d, J=2.1 Hz, 1H), 6.79 (s, 1H), 6.22 (d, J=8.2 Hz, 1H), 5.97 (d, J=2.1 Hz, 1H), 5.36 (s, 2H), 3.99 (s, 3H).

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7e3806b75f1b42be92651472ad24d57a
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

Loading…