Methyl iodide → HCID 67276238, compound

HRID 1698516Notes

Reaction equation

HRID 1698516 reaction equation
[CH3:1][I:2].[Cl:3][C:4]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:5]=1[C:6]([NH:8][CH:9]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH:26]2[CH2:28][CH2:27]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1)[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:7]>CC(C)=O>[I-:2].[CH:26]1([CH2:25][S:22]([C:19]2[CH:18]=[CH:17][C:16]([CH:9]([NH:8][C:6](=[O:7])[C:5]3[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:4]=3[Cl:3])[C:10]3[CH:11]=[N+:12]([CH3:1])[CH:13]=[CH:14][CH:15]=3)=[CH:21][CH:20]=2)(=[O:24])=[O:23])[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 57959873HCID 57959873, compound

Product 1

HCID 67276238HCID 67276238, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl iodide (263 μL, 4.2 mmol) and 2,4-dichloro-N-[{4-[(cyclopropylmethyl)sulphonyl]phenyl}(pyridin-3-yl)methyl]benzamide (prepared as described in Example 53, 200 mg, 0.42 mmol) were stirred in acetone (4 mL) for 16 h under nitrogen. The resulting yellow suspension was concentrated in vacuo to give 3-{{4-[(cyclopropylmethyl)sulphonyl]phenyl}[(2,4-dichlorobenzoyl)amino]methyl}-1-methylpyridinium iodide. The salt was dissolved in methanol (5 mL) and the solution cooled to −10° C. Sodium borohydride (18 mg, 0.47 mmol) was added and the mixture was stirred at −10° C. for 10 mins and then allowed to warm to room temperature, with stirring, over 1 h. The reaction was quenched with 1N NaOH(aq) (20 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated. Purification by chromatography on silica eluting with 5% methanol in dichloromethane (+<0.5% ammonia) was followed by salt formation by treatment with ethereal HCl to give the title compound as a white solid (123 mg, 55% yield). m/z (ES+) 495 (M+H), 493 (M+H).

Workup

  1. concentrationThe resulting yellow suspension was concentrated in vacuo

Sources & evidence

ORD record
ord-7724bec5a9844e139a20525f24916eab
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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