N-(2,2-dimethoxyethyl)cyclopentanamine → N-Cyclopentyl-N-(2,2-dimethoxyethyl)-3-(3-(1-isopropyl-1H-pyrazol-4-yl)phenethoxy)propanamide

HRID 909937Notes

Reaction equation

HRID 909937 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)[CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH3:23][O:24][CH:25]([O:33][CH3:34])[CH2:26][NH:27][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH:28]1([N:27]([CH2:26][CH:25]([O:33][CH3:34])[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[CH:6]=[N:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH:8]=3)[CH:10]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

3

Reactant 2

HCID 58168622N-(2,2-dimethoxyethyl)cyclopentanamineHCID 59290435HCID 59290435, compound

Product 1

HCID 59290440N-Cyclopentyl-N-(2,2-dimethoxyethyl)-3-(3-(1-isopropyl-1H-pyrazol-4-yl)phenethoxy)propanamide

Procedure

The subtitled compound (140 mg) was prepared from 3-(3-(1-isopropyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 20 Step iii)] and N-(2,2-dimethoxyethyl)cyclopentanamine [Preparation 9] using a similar method to that described in Example 18, Step iii). MS [M+H-MeOH]+=426 (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 8.01 and 8.00 (2×s, 1H), 7.79 (s, 1H), 7.40 (s, 1H), 7.36 (d, J=7.9 Hz, 1H), 7.23 (t, J=7.6 Hz, 1H), 7.05 (d, J=7.6 Hz, 1H), 4.56 and 4.37 (2×t, J=5.1 Hz, 1H), 4.53 (septet, J=6.8 Hz, 1H), 4.26-4.16 (m, 1H), 3.76-3.64 (m, 4H), 3.35 and 3.22 (2×d, J=5.1 Hz, 2H), 3.34 (s, 3H), 3.32 (s, 3H), 2.84 (t, J=6.7 Hz, 2H), 2.65 (t, J=6.2 Hz, 2H), 1.82-1.45 (m, 8H), 1.51 (d, J=6.8 Hz, 6H); a ˜2:1 mixture of rotamers is observed.

Workup

  1. additiona ˜2:1 mixture of rotamers

Sources & evidence

ORD record
ord-188e20fcba194cb688633f1fa73f8ec7
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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