N-(2,2-dimethoxyethyl)cyclohexanamine → 3-(3-(2-Allyl-2H-tetrazol-5-yl)phenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

HRID 909924Notes

Reaction equation

HRID 909924 reaction equation
[CH2:1]([N:4]1[N:8]=[N:7][C:6]([C:9]2[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[N:5]1)[CH:2]=[CH2:3].[CH3:23][O:24][CH:25]([O:34][CH3:35])[CH2:26][NH:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH2:1]([N:4]1[N:8]=[N:7][C:6]([C:9]2[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]([N:27]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:26][CH:25]([O:34][CH3:35])[O:24][CH3:23])=[O:19])=[N:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 592903823-(3-(2-allyl-2H-tetrazol-5-yl)phenethoxy)propanoic acid

Product 1

HCID 592904473-(3-(2-Allyl-2H-tetrazol-5-yl)phenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

Procedure

The subtitled compound (450 mg) was prepared from 3-(3-(2-allyl-2H-tetrazol-5-yl)phenethoxy)propanoic acid [Example 7, Step ii)] and N-(2,2-dimethoxyethyl)cyclohexanamine using a similar method to that described in Example 14, Step iii). 1H NMR (300 MHz, CD3OD) δ 8.04-7.92 (m, 2H), 7.49-7.36 (m, 2H), 6.29-6.11 (m, 1H), 5.47-5.30 (m, 4H), 4.56 and 4.39 (2×t, J=5.3 Hz, 1H), 4.09-3.94 (m, 1H), 3.81-3.67 (m, 4H), 3.372 and 3.368 (2×s, 6H), 3.34 and 3.29 (d, J=5.3 Hz, 2H), 3.00-2.91 (m, 2H), 2.72-2.64 (m, 2H), 1.84-1.02 (m, 10H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-91c71eb3630648c09b2a801e0d6610c3
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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