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

HRID 909939Notes

Reaction equation

HRID 909939 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([OH:18])=O)[CH:5]=[N:4]1)[CH3:2].[CH3:22][O:23][CH:24]([O:32][CH3:33])[CH2:25][NH:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:27]1([N:26]([CH2:25][CH:24]([O:32][CH3:33])[O:23][CH3:22])[C:16](=[O:18])[CH2:15][CH2:14][O:13][CH2:12][CH2:11][C:10]2[CH:19]=[CH:20][CH:21]=[C:8]([C:6]3[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[CH:7]=3)[CH:9]=2)[CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 58168622N-(2,2-dimethoxyethyl)cyclopentanamineHCID 592904833-(3-(1-ethyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid

Product 1

HCID 59290486N-Cyclopentyl-N-(2,2-dimethoxyethyl)-3-(3-(1-ethyl-1H-pyrazol-4-yl)phenethoxy)propanamide

Procedure

The subtitled compound (138 mg) was prepared from 3-(3-(1-ethyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 23 Step ii)] and N-(2,2-dimethoxyethyl)cyclopentanamine [Preparation 9] using a similar method to that described in Example 18, Step iii), extending the reaction time to 1 h. MS [M+H-MeOH]+=412 (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 7.97 (s, 1H), 7.79 (s, 1H), 7.40 (s, 1H), 7.35 (d, J=7.5 Hz, 1H), 7.23 (t, J=7.5 Hz, 1H), 7.05 (d, J=7.7 Hz, 1H), 4.56 and 4.37 (2×t, J=5.1 Hz, 1H), 4.26-4.16 (m, 1H), 4.19 (q, J=7.4 Hz, 2H), 3.75-3.64 (m, 4H), 3.35 and 3.22 (2×d, J=4.9 Hz, 2H), 3.34 (s, 3H), 3.32 (s, 3H), 2.84 (t, J=6.8 Hz, 2H), 2.65 (t, J=6.3 Hz, 2H), 1.82-1.44 (m, 8H), 1.47 (t, J=7.3 Hz, 3H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. customto 1 h
  2. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-7eee3e9b1f6644daa470198fd866ffbd
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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