Methyl iodide → HCID 90419149, compound

HRID 530833Notes

Reaction equation

HRID 530833 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][N:7]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:8]2[C:9](=[O:28])[N:10]([CH3:27])[N:11]=[C:12]([O:14][CH2:15][C@H:16]3[CH2:18][C@@H:17]3[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][N:20]=3)[CH:13]=2)[N:3]=[N:2]1.[H-].[Na+].CI.[CH3:42]OC1C=CC(CN(CC2C=NN(C)N=2)C2C(=O)N(C)N=C(OC[C@H]3C[C@@H]3C3C=CC(OC)=CN=3)C=2)=CC=1>C1COCC1.O.CCOC(C)=O>[CH3:37][O:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][N:7]([CH2:6][C:4]2[N:3]=[N:2][N:1]([CH3:42])[CH:5]=2)[C:8]2[C:9](=[O:28])[N:10]([CH3:27])[N:11]=[C:12]([O:14][CH2:15][C@H:16]3[CH2:18][C@@H:17]3[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][N:20]=3)[CH:13]=2)=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90419167HCID 90419167, compoundHCID 178491074HCID 178491074, compound

Product 1

HCID 90419149HCID 90419149, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 2 (100 mg, 0.20 mmol) in THF (20 mL) was added NaH (12 mg, 0.30 mmol) at 0° C. After stirred for 10 min, MeI (57 mg, 0.40 mmol) was added. The mixture was stirred for 2 h at room temperature and then diluted with H2O (20 mL) and EtOAc (50 mL). The organic phase was washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by prep-TLC using PE/EtOAc=4/1 to give 4-((4-methoxybenzyl)((1-methyl-1H-1,2,3-triazol-4-yl)methyl)amino)-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyridazin-3(2H)-one (3) (55 mg, yield: 53%) as a yellow solid and 4-((4-methoxybenzyl)((2-methyl-2H-1,2,3-triazol-4-yl)methyl)amino)-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyridazin-3(2H)-one (4). ESI-MS: 461.2 (M+H)+.

Workup

  1. stirringThe mixture was stirred for 2 h at room temperature
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by prep-TLC using PE/EtOAc=4/1

Sources & evidence

ORD record
ord-0a87bb8b48c444ef96eafdf402f6a338
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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