N-(2,2-dimethoxyethyl)cyclohexanamine → HCID 59290412, compound

HRID 909929Notes

Reaction equation

HRID 909929 reaction equation
[F:1][C:2]1[C:15]([C:16]2[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=2)=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]([OH:11])=O.[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:9](=[O:11])[CH2:8][CH2:7][O:6][CH2:5][CH2:4][C:3]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)[C:2]=2[F:1])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 59290367HCID 59290367, compound

Product 1

HCID 59290412HCID 59290412, compound

Procedure

The subtitled compound (1.6 g) was prepared form 3-(2-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 16, 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 7.97 (s, 1H), 7.84 (d, J=2.3 Hz, 1H), 7.46 (td, J=2.0 and 7.6 Hz, 1H), 7.15-7.02 (m, 2H), 4.53 and 4.37 (2×t, J=5.4 Hz, 1H), 4.04-3.94 and 3.70-3.60 (2×m, 1H), 3.92 (s, 3H), 3.76-3.64 (m, 4H), 3.35 and 3.33 (2×s, 6H), 3.36-3.26 (m, 2H), 2.95-2.88 (m, 2H), 2.65 and 2.63 (2×t, J=6.3 Hz, 2H), 1.81-1.00 (m, 10H); a ˜1:1 mixture of rotamers is observed.

Workup

  1. additiona ˜1:1 mixture of rotamers

Sources & evidence

ORD record
ord-1b1c4232d9954f99aa39b57686b8b8c3
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

Loading…