Dimethylamine → HCID 58974647, compound

HRID 1178211Notes

Reaction equation

[CH3:1][N:2]([CH3:11])[C:3]1[S:7][C:6]([C:8](=O)[CH3:9])=[N:5][CH:4]=1.[CH3:12]NC.BrC1SC(C(=O)C)=NC=1.[N+]([O-])([O-])=O.[CH3:28][C:29]1[CH:30]=[C:31]([NH:36][C:37]([NH2:39])=[NH2+:38])[CH:32]=[C:33]([CH3:35])[CH:34]=1>>[CH3:1][N:2]([CH3:11])[C:3]1[S:7][C:6]([C:8]2[CH:9]=[CH:12][N:39]=[C:37]([NH:36][C:31]3[CH:30]=[C:29]([CH3:28])[CH:34]=[C:33]([CH3:35])[CH:32]=3)[N:38]=2)=[N:5][CH:4]=1

Participants

Reactant 4

HCID 674Dimethylamine

HCID 299397331-(5-Bromo-1,3-thiazol-2-yl)ethan-1-one

HCID 45086499HCID 45086499, compound

HCID 178425132HCID 178425132, compound

Product 1

HCID 58974647HCID 58974647, compound

Procedure

This compound was prepared from 1-(5-Dimethylamino-thiazol-2-yl)-ethanone (prepared from dimethylamine and 1-(5-Bromo-thiazol-2-yl)-ethanone in a procedure similar to that described in method I) and N-(3,5 dimethylphenyl) guanidinium nitrate (prepared using a procedure similar to that described in WO9719065) using procedures similar to those described in methods E-F. The product was isolated as a yellow solid (40% last step); IR (solid) 1738, 1365, 1217, cm−1; 1H NMR (400 Mhz, CDCl3) δ 2.35 (6H, s), 3.1 (6H, s), 6.75 (1H, s), 7.00 (1H, s), 7.37 (1H, s), 7.4 (2H, s), 8.45 (1H, d);); MS (ES+) 326.2 (M+1), (ES−) 324.2 (M−1).

Workup

customprepared
customThe product was isolated as a yellow solid (40% last step)

Sources & evidence

ORD record: ord-1a8ebb4b788d47fd9d5effa2739075de
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276502B2

Reaction notes

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