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1-Hydroxybenzotriazole → tert-Butyl cis(+/-)-3-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate

HRID 1424956
Notes
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Reaction equation

HRID 1424956 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=2)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4][C@H:3]1[O:21][CH3:22].[CH2:23]([C:25]1[NH:29][C:28]([C:30](O)=[O:31])=[N:27][C:26]=1[C:33]([F:36])([F:35])[F:34])[CH3:24].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH2:23]([C:25]1[NH:29][C:28]([C:30]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=3)[C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:4][C@H:3]2[O:21][CH3:22])=[O:31])=[N:27][C:26]=1[C:33]([F:35])([F:36])[F:34])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675485585-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid2×HCID 86648499tert-Butyl cis(+/-)-3-(4-amino-3-methoxypiperidin-1-yl)benzoate

Product 1

HCID 86648498
tert-Butyl cis(+/-)-3-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate
Yield 67%

Procedure

The same operation as in Example (1g) was performed using tert-butyl cis(±)-3-(4-amino-3-methoxypiperidin-1-yl)benzoate obtained in Example (42d) (about 0.26 mmol), 5-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid obtained by the method described in Example (39e) (50 mg, 0.24 mmol), WSC hydrochloride (137 mg, 0.71 mmol) and HOBT (32 mg, 0.24 mmol), to obtain 79.7 mg of the title compound as a white solid (67%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-874b66d557d54234a4ad6d6313f5ac28
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927588B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes