N-(2,2-dimethoxyethyl)cyclohexanamine → HCID 59290406, compound

HRID 909946Notes

Reaction equation

HRID 909946 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]([CH:21]=[CH:22][CH:23]=2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]([OH:20])=O)[CH:7]=[N:6]1.[CH3:24][O:25][CH:26]([O:35][CH3:36])[CH2:27][NH:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:29]1([N:28]([CH2:27][CH:26]([O:35][CH3:36])[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][CH2:3][O:2][CH3:1])[CH:9]=3)[CH:11]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 592903703-(3-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)phenethoxy)propanoic acid

Product 1

HCID 59290406HCID 59290406, compound

Procedure

The subtitled compound (267 mg) was prepared from 3-(3-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 36 Step ii)] and N-(2,2-dimethoxyethyl)cyclohexanamine using a similar method to that described in Example 18, Step iii). MS [M+H-MeOH]+=456 (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 7.95 (s, 1H), 7.81 and 7.80 (2×s, 1H), 7.40-7.37 (m, 1H), 7.35 (d, J=7.7 Hz, 1H), 7.23 and 7.22 (2×t, J=7.7 Hz, 1H), 7.05 (d, J=7.9 Hz, 1H), 4.52 and 4.36 (2×t, J=5.3 Hz, 1H), 4.30 (t, J=5.2 Hz, 2H), 4.04-3.95 and 3.69-3.60 (2×m, 1H), 3.77-3.63 (m, 6H), 3.34 (s, 3H), 3.32 (s, 3H), 3.31 (s, 3H), 3.34 and 3.25 (2×d, J=5.1 Hz, 2H), 2.87-2.81 (m, 2H), 2.67-2.60 (m, 2H), 1.93-0.99 (m, 10H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-5ead2741bda744de8548190c63fb9f79
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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