Methyl iodide → HCID 68291105, compound

HRID 1408993Notes

Reaction equation

HRID 1408993 reaction equation
[CH2:1]([S:3][C:4]1[C:5]2[N:6]([CH:13]=[C:14]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[CH:15]=2)[N:7]=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])[CH3:2].[C:21]([O-])([O-])=O.[K+].[K+].CI.CCOC(C)=O>CN1C(=O)CCC1>[CH2:1]([S:3][C:4]1[C:5]2[N:6]([CH:13]=[C:14]([C:16]3[N:17]=[N:18][N:19]([CH3:21])[N:20]=3)[CH:15]=2)[N:7]=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178477295HCID 178477295, compound

Product 1

HCID 68291105HCID 68291105, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 4-(ethylthio)-6-(1H-tetrazol-5-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (164 mg, 0.567 mmol) in NMP (2.0 mL) were added K2CO3 (196 mg, 1.417 mmol) and MeI (0.043 mL, 0.680 mmol). The solution was stirred at 23° C. for 1 hr. To the reaction mixture was added 30 mL of EtOAc which was washed with 10% LiCl solution (2×10 mL), 10 mL of brine and dried over Na2SO4. Filtration and concentration yielded a crude product which was purified on silica gel column with EtOAc to afford the desired product (64 mg, 35% yield). MS (ES+) m/z: 304.08 (M+H); HPLC retention time: 2.180 min (analytical HPLC Method F).

Workup

  1. washwas washed with 10% LiCl solution (2×10 mL), 10 mL of brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and concentration
  4. customyielded a crude product which
  5. customwas purified on silica gel column with EtOAc

Sources & evidence

ORD record
ord-503dcbffd42c4d7b8af1cf9faabd1192
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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