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

HRID 522572Notes

Reaction equation

HRID 522572 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:27]=[CH:26][C:16]([CH2:17][NH:18]C(=O)OC(C)(C)C)=[CH:15][CH:14]=2)[S:11][CH:12]=1)=[O:7].C(Cl)[Cl:36].Cl>O1CCOCC1>[ClH:36].[NH2:18][CH2:17][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[S:11][CH:12]=[C:8]([C:6]([C:5]3[CH:28]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:7])[N:9]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 53363957tert-Butyl 4-(4-(3,4,5-trimethoxybenzoyl)thiazol-2-yl)benzylcarbamate

Product 1

HCID 53363958(2-(4-(Aminomethyl)phenyl)thiazol-4-yl)(3,4,5-trimethoxyphenyl)methanone hydrochlorideYield 81.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

At 0° C., to a solution of 68a (200 mg) in 10 ml, CH2Cl2 was added a solution of HCl in 1,4-dioxane (4 N, 2 mL) and stirred at RT for 4 h. The precipitate (2r) was filtered and washed with diethyl ether. Yield: 81.3%. 1H NMR (500 MHz, DMSO-d6) δ 8.68 (s, 1H), 8.38 (br, 3H), 8.10 (d, 2H, J=8.4 Hz), 7.66 (d, 2H, J=8.4 Hz), 7.62 (s, 2H), 4.11 (s, 2H), 3.87 (s, 6H), 3.80 (s, 3H). MS (ESI) m/z 385.1 (M+H)+.

Workup

  1. filtrationThe precipitate (2r) was filtered
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-aa4d4e42ee114f76bc9c721628df57e2
Source dataset
uspto-grants-2016_05
Patent number
US09334242B2

Reaction notes

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