Hydrogen chloride-ethyl acetate → HCID 86648865, compound

HRID 1425454Notes

Reaction equation

HRID 1425454 reaction equation
[ClH:1].C(OCC)(=O)C.[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][C@H:19]2[CH2:24][CH2:23][N:22]([C:25]3[S:26][C:27]([C:31]([NH:33][CH:34]4[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]4)=[O:32])=[C:28]([CH3:30])[N:29]=3)[CH2:21][C@H:20]2[O:47][CH3:48])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15]>CO>[ClH:8].[ClH:1].[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][C@H:19]2[CH2:24][CH2:23][N:22]([C:25]3[S:26][C:27]([C:31]([NH:33][CH:34]4[CH2:35][CH2:36][NH:37][CH2:38][CH2:39]4)=[O:32])=[C:28]([CH3:30])[N:29]=3)[CH2:21][C@H:20]2[O:47][CH3:48])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86648864tert-Butyl cis(+/-)-4-({[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazol-5-yl]carbonyl}amino)piperidine-1-carboxylate

Product 1

HCID 86648865HCID 86648865, compoundYield 144.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4 N hydrochloric acid/ethyl acetate solution (2 ml, 8 mmol) was added to a solution of tert-butyl cis(±)-4-({[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazol-5-yl]carbonyl}amino)piperidine-1-carboxylate obtained in Example (266a) (30 mg, 0.05 mmol) in methanol (0.4 mL), followed by stirring for 30 minutes. The solvent was evaporated under reduced pressure. The residue was solidified by adding ethyl acetate, diethyl ether and hexane, to obtain 21 mg of the title compound as a cream-colored solid (72%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionby adding ethyl acetate, diethyl ether and hexane

Sources & evidence

ORD record
ord-b1a3d2ce5f074e7fb7e99f3b46c0d656
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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