N-(2,2-dimethoxyethyl)cyclohexanamine → N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide

HRID 909930Notes

Reaction equation

HRID 909930 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([C:16]2[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=2)[CH:15]=1)[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([OH:12])=O.[CH3:22][O:23][CH:24]([O:33][CH3:34])[CH2:25][NH:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:27]1([N:26]([CH2:25][CH:24]([O:33][CH3:34])[O:23][CH3:22])[C:10](=[O:12])[CH2:9][CH2:8][O:7][CH2:6][CH2:5][C:4]2[CH:13]=[C:14]([C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)[CH:15]=[C:2]([F:1])[CH:3]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 592904703-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid

Product 1

HCID 59290454N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide

Procedure

The subtitled compound (3.3 g) was prepared from 3-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 17, Step v)] and N-(2,2-dimethoxyethyl)cyclohexanamine using a similar method to that described in Example 12, Step iii). MS [M+H-MeOH]+=430 (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 7.97 (s, 1H), 7.81 and 7.80 (2×s, 1H), 7.19 (m, 1H), 7.09 (dt, J=10.0, 1.9 Hz, 1H), 6.80 (m, 1H), 4.52 and 4.36 (2×t, J=5.0 Hz, 1H), 4.00 and 3.64 (2×tt, J=3.6 and 11.7 Hz, 1H), 3.902 and 3.898 (2×s, 3H), 3.76-3.64 (m, 4H), 3.34 (s, 3H), 3.33 and 3.25 (2×d, J=5.1 Hz, 2H), 3.32 (s, 3H), 2.85 and 2.84 (2×t, J=6.2 Hz, 2H), 2.65 and 2.63 (2×t, J=6.1 Hz, 2H), 1.79-1.69 (m, 2H), 1.68-1.49 (m, 3H), 1.49-1.19 (m, 4H), 1.16-1.01 (m, 1H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-6a3a32a8fddb496389a61a97fde5d500
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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