Sodium Carbonate → Ethyl trans(+/-)-2-[3-(butylamino)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl]-1,3-benzothiazole-7-carboxylate

HRID 43535Notes

Reaction equation

HRID 43535 reaction equation
[CH2:1]([NH:5][C@H:6]1[C@H:11]([NH:12][C:13]([C:15]2[NH:16][C:17]([CH2:21][CH3:22])=[C:18]([Cl:20])[N:19]=2)=[O:14])[CH2:10][CH2:9][N:8]([C:23]2[S:24][C:25]3[C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)[CH2:7]1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+].BrC1S[C:44]2C(C(OCC)=O)=CC=C[C:45]=2N=1>>[CH2:1]([NH:5][C@H:6]1[C@H:11]([NH:12][C:13]([C:15]2[NH:16][C:17]([CH2:21][CH3:22])=[C:18]([Cl:20])[N:19]=2)=[O:14])[CH2:10][CH2:9][N:8]([C:23]2[S:24][C:25]3[C:31]([C:32]([O:34][CH2:44][CH3:45])=[O:33])=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)[CH2:7]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 60135941HCID 60135941, compoundHCID 67073467Ethyl 2-bromobenzo[d]thiazole-7-carboxylate2×

Product 1

HCID 86648546Ethyl trans(+/-)-2-[3-(butylamino)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl]-1,3-benzothiazole-7-carboxylateYield 76%

Procedure

The same operation as in Example (1h) was performed using tert-butyl trans(±)-3-(butylamino)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidine-1-carboxylate obtained in Example (77d) (16.3 mg, 0.038 mmol), sodium carbonate (40 mg, 0.38 mmol) and ethyl 2-bromo-1,3-benzothiazole-7-carboxylate obtained by the method described in Example (1f) (13.2 mg, 0.046 mmol), to obtain 15.5 mg of the title compound (76%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-b0e2effd0ee64251a511624f572fa812
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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