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Hydrochloric Acid → 3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-N-[5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2yl]-propionamide hydrochloride

HRID 1689571
Notes
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Reaction equation

HRID 1689571 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][C:22](=[O:41])[NH:23][C:24]1[S:25][C:26]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([S:37]([CH3:40])(=[O:39])=[O:38])[CH:31]=2)=[C:27]([CH3:29])[N:28]=1)(C)(C)C.Cl>ClCCl>[ClH:36].[NH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][C:22]([NH:23][C:24]1[S:25][C:26]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([S:37]([CH3:40])(=[O:38])=[O:39])[CH:31]=2)=[C:27]([CH3:29])[N:28]=1)=[O:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86639506(2-{2-[2-(2-{2[5-(4-Chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylcarbamoyl]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 866395073-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-N-[5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2yl]-propionamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

(2-{2-[2-(2-{2[5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylcarbamoyl]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-carbamic acid tert-butyl ester (1.0 g 1.5 mmol) was dissolved in dichloromethane (10 ml) and treated with HCl (4 ml 4M solution in dioxane). The reaction was stirred at room temperature for 3 hours. The solvent was evaporated and the residue dried under vacuum to yield 3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-N-[5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2yl]-propionamide hydrochloride as a yellow viscous oil (830 mg residual solvent present) 1H NMR (400 MHz CDCl3) 8.4 (br s, 3H), 8.2 (s, 1H), 7.7 (br d, 1H), 7.6 (br d, 1H) 3.9 (br m, 4H), 3.8-3.6 (br m, 12H), 3.3 (s, 3H), 3.3 (br m, 2H), 3.1 (br m, 2H), 2.6 (s, 3H). NMR spectra were obtained on a Bruker dpx400.

Workup

  1. customThe solvent was evaporated
  2. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-d6ef85e2f0a94f1bb7aa126116d6dcd3
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153389B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes