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

HRID 43544

Reaction equation

[NH2:1][C@H:2]1[C@@H:7]([NH:8][C:9]([C:11]2[NH:12][C:13]([CH2:17][CH3:18])=[C:14]([Cl:16])[N:15]=2)=[O:10])[CH2:6][CH2:5][N:4]([C:19]2[S:20][C:21]3[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)[CH2:3]1.[CH:33]1([CH:36]=O)[CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Cl:16][C:14]1[N:15]=[C:11]([C:9]([NH:8][C@H:7]2[CH2:6][CH2:5][N:4]([C:19]3[S:20][C:21]4[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)[CH2:3][C@H:2]2[NH:1][CH2:36][CH:33]2[CH2:35][CH2:34]2)=[O:10])[NH:12][C:13]=1[CH2:17][CH3:18]

Participants

Reactant 3

HCID 123114Cyclopropanecarboxaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 86648558Ethyl cis(+/-)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate2×

Product 1

HCID 86648561Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-[(cyclopropylmethyl)amino]piperidin-1-yl)-1,3-benzothiazole-7-carboxylateYield 93%

Procedure

The same operation as in Example (77d) was performed using ethyl cis(±)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate obtained by the method described in Example (81e) (37 mg, 0.071 mmol), cyclopropanecarbaldehyde (6.5 μL, 0.087 mmol) and sodium (triacetoxy)borohydride (44 mg, 0.21 mmol), to obtain 35.3 mg of the title compound as a white solid (93%).

Workup

customobtained by the method

Sources & evidence

ORD record: ord-972cdf58305a4dd4a3f2434fd8e8fd19
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Linked notes

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