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

HRID 909933Notes

Reaction equation

HRID 909933 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]([CH:21]=[CH:22][CH:23]=3)[CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]([OH:20])=O)[CH:7]=[N:6]2)[CH2:3][CH2:2]1.[CH3:24][O:25][CH:26]([O:34][CH3:35])[CH2:27][NH:28][CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:29]1([N:28]([CH2:27][CH:26]([O:34][CH3:35])[O:25][CH3:24])[C:18](=[O:20])[CH2:17][CH2:16][O:15][CH2:14][CH2:13][C:12]2[CH:21]=[CH:22][CH:23]=[C:10]([C:8]3[CH:7]=[N:6][N:5]([CH2:4][CH:1]4[CH2:2][CH2:3]4)[CH:9]=3)[CH:11]=2)[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

3

Reactant 2

HCID 58168622N-(2,2-dimethoxyethyl)cyclopentanamineHCID 592903693-(3-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)phenethoxy)propanoic acid

Product 1

HCID 59290362N-Cyclopentyl-3-(3-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)phenethoxy)-N-(2,2-dimethoxyethyl)propanamide

Procedure

The subtitled compound (246 mg) was prepared from 3-(3-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 19, Step iii)] and N-(2,2-dimethoxyethyl)cyclopentanamine, prepared as in Preparation 9 using a similar method to that described in Example 18, Step iii). MS [M+H-MeOH]+=438 (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 8.01 (s, 1H), 7.79 (s, 1H), 7.40 (s, 1H), 7.36 (d, J=7.7 Hz, 1H), 7.23 (t, J=7.8 Hz, 1H), 6.96 (d, J=7.7 Hz, 1H), 4.56 and 4.37 (2×t, J=5.4 Hz, 1H), 4.26-4.15 (m, 1H), 4.00 (d, J=6.9 Hz, 2H), 3.76-3.65 (m, 4H), 3.35 and 3.22 (2×d, J=4.8 Hz, 2H), 3.34 (s, 3H), 3.32 (s, 3H), 2.85 (t, J=6.4 Hz, 2H), 2.65 (t, J=6.3 Hz, 2H), 1.82-1.44 (m, 8H), 1.38-1.23 (m, 1H), 0.65-0.57 (m, 2H), 0.44-0.33 (m, 2H), a ˜1:1 mixture of rotamers is observed.

Sources & evidence

ORD record
ord-58456a8ff79a48b79bbb097fe665afe9
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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