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

HRID 909914Notes

Reaction equation

HRID 909914 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([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:6]=[N:5]1)([CH3:3])[CH3:2].[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.C(OCC)(=O)C>CCCC(C)C>[CH:28]1([N:27]([CH2:26][CH:25]([O:34][CH3:35])[O:24][CH3:23])[C:17](=[O:19])[CH2:16][CH2:15][O:14][CH2:13][CH2:12][C:11]2[CH:20]=[CH:21][CH:22]=[C:9]([C:7]3[N:6]=[N:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH:8]=3)[CH:10]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 59290472HCID 59290472, compound

Product 1

HCID 59290386N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1-isopropyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanamide

Reagents, catalysts & solvents 1

HCID 78922-MethylpentaneSolvent

Procedure

The subtitled compound (230 mg) was prepared from 3-(3-(1-isopropyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoic acid [Example 12, Step ii)] and N-(2,2-dimethoxyethyl)cyclohexanamine using a similar method to that described in Example 4, Step v) and the elution gradient to 0 to 100% ethyl acetate in isohexane. MS [M+H-MeOH]+=441 (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 8.36 (s, 1H), 7.71-7.61 (m, 2H), 7.32 and 7.31 (2×t, J=7.7 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 4.87 (septet, J=6.7 Hz, 1H), 4.51 and 4.36 (2×t, J=5.4 Hz, 1H), 4.03-3.94 and 3.69-3.60 (2×m, 1H), 3.76-3.66 (m, 4H), 3.34 and 3.25 (2×d, J=5.3 Hz, 2H), 3.34 (s, 3H), 3.31 (s, 3H), 2.91-2.85 (m, 2H), 2.68-2.61 (m, 2H), 1.79-1.01 (m, 10H), 1.61 (d, J=6.8 Hz, 6H), a ˜1:1 mixture of rotamers is observed.

Sources & evidence

ORD record
ord-eca2938e76f9419383d54cdd10e47d11
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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