Sodium Bicarbonate → Ethyl trans(+/-)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 43540Notes

Reaction equation

HRID 43540 reaction equation
Br.C(O)(=O)C.C(OC([NH:16][C@H:17]1[C@H:22]([NH:23][C:24]([C:26]2[NH:27][C:28]([CH2:32][CH3:33])=[C:29]([Cl:31])[N:30]=2)=[O:25])[CH2:21][CH2:20][N:19]([C:34]2[S:35][C:36]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:37]([CH3:39])[N:38]=2)[CH2:18]1)=O)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>>[NH2:16][C@H:17]1[C@H:22]([NH:23][C:24]([C:26]2[NH:27][C:28]([CH2:32][CH3:33])=[C:29]([Cl:31])[N:30]=2)=[O:25])[CH2:21][CH2:20][N:19]([C:34]2[S:35][C:36]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:37]([CH3:39])[N:38]=2)[CH2:18]1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86648553Ethyl trans(+/-)-2-(3-{[(benzyloxy)carbonyl]amino}-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate2×

Product 1

HCID 86648554Ethyl trans(+/-)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylateYield 100%

Procedure

Hydrobromic acid/acetic acid solution (1 mL) was added to ethyl trans(±)-2-(3-{[(benzyloxy)carbonyl]amino}-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained by the method described in Example (79e) (62 mg, 0.11 mmol), and the mixture was stirred for 25 minutes. Saturated aqueous sodium bicarbonate solution was added to the reaction solution. Purification by reverse phase silica gel chromatography (elution solvent: distilled water, distilled water/THF=70/30, 60/40) gave 51.3 mg of the title compound (100%).

Workup

  1. customobtained by the method
  2. customPurification
  3. washby reverse phase silica gel chromatography (elution solvent: distilled water, distilled water/THF=70/30, 60/40)

Sources & evidence

ORD record
ord-58a9810d3f124635be795b7e12f7307c
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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