Methyl iodide → 4-[4-{[(Benzyloxy)carbonyl]amino}-3-(propan-2-yloxy)phenyl]-3-methoxy-1-methylpyridinium iodide

HRID 518804Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3.58 g of benzyl [4-(3-methoxypyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate and 1.14 ml of methyl iodide in 107 ml of acetone is heated at 50° C. (bath) for 1 h. 568 μl of methyl iodide are added and the heating is continued at 50° C. for 30 minutes. The mixture is then concentrated under vacuum, so as to give 4.57 g of 4-[4-{[(benzyloxy)carbonyl]amino}-3-(propan-2-yloxy)phenyl]-3-methoxy-1-methylpyridinium iodide in the form of a yellow solid.

Workup

concentrationThe mixture is then concentrated under vacuum

Sources & evidence

ORD record: ord-06e24784884f48ff8960c8a1a44ba1f2
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Reaction notes

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