N-(2,2-dimethoxyethyl)cyclohexanamine → HCID 59290366, compound

HRID 909919Notes

Reaction equation

HRID 909919 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:4][C:3]=1[C:16]1[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=1.[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:11](=[O:13])[CH2:10][CH2:9][O:8][CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][C:2]([F:1])=[C:3]([C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)[CH:4]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 59290427HCID 59290427, compound

Product 1

HCID 59290366HCID 59290366, compound

Procedure

The subtitled compound (3.3 g) was prepared from 3-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 13, 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 7.99 and 7.98 (2×s, 1H), 7.86 (and 7.85 (2×s, 1H), 7.47 (m, 1H), 7.09-6.97 (m, 2H), 4.51 and 4.36 (2×t, J=5.4 Hz, 1H), 4.00 and 3.62 (tt, J=3.2 and 12.0 Hz, 1H), 3.920 and 3.918 (2×s, 3H), 3.75-3.63 (m, 4H), 3.34 (s, 3H), 3.33 (d, J=5.6 Hz, 1H), 3.32 (s, 3H), 3.25 (d, J=5.2 Hz, 1H), 2.86-2.79 (m, 2H), 2.65 and 2.63 (2×t, J=6.1 Hz, 2H), 1.79-1.01 (m, 10H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-5c65462fd20a425393dc1f5f23f63b82
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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