Ethyl Acetate → 3-(3-(1-Allyl-1H-1,2,3-triazol-4-yl)phenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

HRID 909921Notes

Reaction equation

HRID 909921 reaction equation
[CH2:1]([N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]([O:19]C(C)(C)C)=O)[N:6]=[N:5]1)[CH:2]=[CH2:3].[CH3:27][O:28][CH:29]([O:38][CH3:39])[CH2:30][NH:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C(OCC)(=O)C>CCCC(C)C>[CH2:1]([N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]([N:31]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:30][CH:29]([O:38][CH3:39])[O:28][CH3:27])=[O:19])[N:6]=[N:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 59290465tert-Butyl 3-(3-(1-allyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoate

Product 1

HCID 592904813-(3-(1-Allyl-1H-1,2,3-triazol-4-yl)phenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

Reagents, catalysts & solvents 1

HCID 78922-MethylpentaneSolvent

Procedure

The subtitled compound (584 mg) was prepared from tert-butyl 3-(3-(1-allyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoate [Ex 4, Step iii)] and N-(2,2-dimethoxyethyl)cyclohexanamine using a similar method to that described in Example 12, Step iii) the elution gradient 20 to 100% ethyl acetate in isohexane. 1H NMR (400 MHz, CD3OD) δ 8.29 (s, 1H), 7.69 and 7.67 (2 s, 1H), 7.64 (d, J=7.9 Hz, 1H), 7.322 and 7.318 (2×t, J=7.7 Hz, 1H), 7.20 (d, J=6.9 Hz, 1H), 6.17-6.06 (m, 1H), 5.36-5.27 (m, 2H), 5.06 (d, J=5.9 Hz, 2H), 4.52 and 4.36 (2×t, J=5.5 Hz, 1H), 3.99 and 3.65 (tt, J=5.3 and 11.7 Hz, 1H), 3.76-3.66 (m, 4H), 3.34 (s, 3H), 3.32 (s, 3H), 3.34 and 3.25 (2×d, J=4.9 Hz, 2H), 2.92-2.85 (m, 2H), 2.68-2.61 (m, 2H), 1.79-1.02 (m, 10H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-ce8395a1fc7f4664b9c042df82c0fdd6
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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