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 1425012Notes

Reaction equation

HRID 1425012 reaction equation
Br.C(O)(=O)C.CC1N=CSC=1C([O-])=O.C(OC([NH:25][C@H:26]1[C@H:31]([NH:32][C:33]([C:35]2[NH:36][C:37]([CH2:41][CH3:42])=[C:38]([Cl:40])[N:39]=2)=[O:34])[CH2:30][CH2:29][N:28]([C:43]2[S:44][C:45]([C:49]([O:51][CH2:52][CH3:53])=[O:50])=[C:46]([CH3:48])[N:47]=2)[CH2:27]1)=O)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>>[NH2:25][C@H:26]1[C@H:31]([NH:32][C:33]([C:35]2[NH:36][C:37]([CH2:41][CH3:42])=[C:38]([Cl:40])[N:39]=2)=[O:34])[CH2:30][CH2:29][N:28]([C:43]2[S:44][C:45]([C:49]([O:51][CH2:52][CH3:53])=[O:50])=[C:46]([CH3:48])[N:47]=2)[CH2:27]1

Participants

5

Reactant 4

HCID 516892Sodium BicarbonateHCID 6920190HCID 6920190, compoundHCID 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-carboxylate

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 105.8%

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-2e1abc519c254984a8ead2839666aef6
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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