Hydrochloric Acid → 2-(3-methylamino-propyl)-thiazole-4-carboxylic acid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide hydrochloride salt

HRID 470722Notes

Reaction equation

HRID 470722 reaction equation
C(O[C:6](=O)[N:7](C)[CH2:8][CH2:9][CH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:29])[N:17]([CH3:28])[C@H:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][CH2:20][CH2:19]2)[N:15]=1)(C)(C)C.[ClH:32]>O1CCOCC1>[ClH:32].[CH3:28][N:17]([C@H:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][CH2:19]1)[C:16]([C:14]1[N:15]=[C:11]([CH2:10][CH2:9][CH2:8][NH:7][CH3:6])[S:12][CH:13]=1)=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67252275methyl-{3-[4-((R)-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl-carbamoyl)-thiazol-2-yl]-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 672534412-(3-methylamino-propyl)-thiazole-4-carboxylic acid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide hydrochloride saltYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl-{3-[4-((R)-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl-carbamoyl)-thiazol-2-yl]-propyl}-carbamic acid tert-butyl ester (0.133 g, 0.3 mmol) was added a solution of 1M HCl in dioxane (0.65 mL) at RT. After stirring overnight at RT, the solvent was evaporated under reduce pressure. The resulting solid was triturated with diethylether, and filtered to give 2-(3-methylamino-propyl)-thiazole-4-carboxylic acid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide hydrochloride salt (0.097 g, 94%). 1H-NMR (400 MHz, CDCl3): δ=9.82-9.58 (br, 2H), 7.79 (s, 1H (conformers)), 7.12-7.03 (m, 4H), 5.43-5.54 (m, 1H (conformers)), 3.45-3.22 (m, 2H), 3.21-3.02 (m, 2H), 2.98-2.64 (m, 5H), 2.61-2.24 (m, 5H), 2.22-1.66 (m, 4H). MS: m/z=330 (M+1). MS: m/z=344 (M+1).

Workup

  1. customthe solvent was evaporated
  2. customThe resulting solid was triturated with diethylether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b84fb67334954f8e926e913495072be1
Source dataset
uspto-grants-2014_01
Patent number
US08629286B2

Reaction notes

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