tert-Butyl 4-(methylamino)benzoate → tert-Butyl-4-[{7-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-7-oxoheptyl}(methyl)amino]benzoate

HRID 446536Notes

Reaction equation

HRID 446536 reaction equation
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:29])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]O)[CH3:19])[CH2:12][CH2:11]1.[CH3:36][NH:37][C:38]1[CH:50]=[CH:49][C:41]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[CH:40][CH:39]=1>>[C:45]([O:44][C:42](=[O:43])[C:41]1[CH:49]=[CH:50][C:38]([N:37]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]([N:18]([CH2:17][CH2:16][N:13]2[CH2:14][CH2:15][CH:10]([O:9][C:8](=[O:29])[NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:11][CH2:12]2)[CH3:19])=[O:28])[CH3:36])=[CH:39][CH:40]=1)([CH3:47])([CH3:46])[CH3:48]

Participants

3

Reactant 2

HCID 22291264tert-Butyl 4-(methylamino)benzoateHCID 666716911-{2-[(7-Hydroxyheptanoyl)(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

Product 1

HCID 66793798tert-Butyl-4-[{7-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-7-oxoheptyl}(methyl)amino]benzoateYield 26%

Procedure

The compound (163 mg, 0.338 mmol) obtained in Example 39b was used according to the method described in Example 4g to give a crude aldehyde compound (160 mg). The resulting crude aldehyde compound and the compound (69 mg, 0.334 mmol) obtained in Example 35a were used a to give the title compound (58 mg; yield, 26%) as a white solid according to the method described in Example 18b.

Workup

  1. customto give a crude aldehyde compound (160 mg)

Sources & evidence

ORD record
ord-b9877a9894fa46bf9c25d28370f9c3f3
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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