Hydrochloric Acid → (2-(4-((Methylamino)methyl)phenyl)thiazol-4-yl)(3,4,5-trimethoxyphenyl)methanone hydrochloride

HRID 522574Notes

Reaction equation

HRID 522574 reaction equation
[CH3:1][N:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][CH:19]=[C:20]([C:22](=[O:35])[C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)[N:21]=2)=[CH:13][CH:12]=1)C(=O)OC(C)(C)C.[ClH:36]>C(Cl)Cl.O1CCOCC1>[ClH:36].[CH3:1][NH:2][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[S:18][CH:19]=[C:20]([C:22]([C:23]3[CH:24]=[C:25]([O:33][CH3:34])[C:26]([O:31][CH3:32])=[C:27]([O:29][CH3:30])[CH:28]=3)=[O:35])[N:21]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53363962HCID 53363962, compound

Product 1

HCID 53363960(2-(4-((Methylamino)methyl)phenyl)thiazol-4-yl)(3,4,5-trimethoxyphenyl)methanone hydrochlorideYield 81.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

At 0° C., to a solution of 71a (60 mg) in 5 mL CH2Cl2 was added a solution of HCl in 1,4-dioxane (4 N, 2 mL) and stirred at RT for overnight. The precipitate (2s-HCl) was filtered and washed with diethyl ether. Yield: 81.3%. 1H NMR (500 MHz, CDCl3) δ 10.0 (s, 1H), 8.29 (s, 1H), 8.05 (d, 2H, J=6.0 Hz), 7.74 (s, 2H), 7.72 (d, 2H, J=6.0 Hz), 4.15 (s, 2H), 3.99 (s, 3H), 3.96 (s, 6H), 2.61 (s, 3H). MS (ESI) m/z 399.1 (M+H)+.

Workup

  1. filtrationThe precipitate (2s-HCl) was filtered
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-39a61000e4e1408597d5cf3b6ac24598
Source dataset
uspto-grants-2016_05
Patent number
US09334242B2

Reaction notes

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