Lithium Hydroxide → HCID 118366241, compound

HRID 59914Notes

Reaction equation

HRID 59914 reaction equation
[CH2:1]([O:3][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[C:21]([F:22])=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].[NH2:27][C@H:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C:33]([O:35]C)=[O:34].CCN=C=NCCCN(C)C.Cl.[Li+].[OH-]>>[CH2:1]([O:3][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[C:21]([F:22])=[CH:20][C:16]([C:17]([NH:27][C@H:28]3[CH2:32][CH2:31][CH2:30][C@H:29]3[C:33]([OH:35])=[O:34])=[O:18])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2]

Participants

5

Reactant 4

HCID 3939Lithium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14698811methyl (1R,2S)-2-aminocyclopentane-1-carboxylateHCID 118366159(R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)-5-fluoronicotinic acid

Product 1

HCID 118366241HCID 118366241, compound

Procedure

(1R,2S)-2-(6-((R)-3-(2-ethoxyphenoxy)piperidin-1-yl)-5-fluoronicotinamido)cyclopentane-1-carboxylic acid was prepared from (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)-5-fluoronicotinic acid and methyl (1R,2S)-2-aminocyclopentane-1-carboxylate using Amidation Method 2 (EDCl) and Ester Hydrolysis Method 1 (LiOH). 1H NMR (400 MHz, DMSO-d6) δ 11.3 (s, 1H), 8.35 (s, 1H), 7.59 (dd, 1H), 7.03 (d, 1H), 6.91 (m, 3H), 4.38 (m, 1H), 4.05 (dd, 1H), 3.93 (m, 3H), 3.69 (m, 1H), 3.50 (m, 2H), 2.33 (m, 1H), 1.98 (m, 4H), 1.79 (m, 1H), 1.60 (m, 3H), 1.45 (m, 2H), 1.25 (t, 3H). MS (ES+) 472.0 (M+H).

Sources & evidence

ORD record
ord-ea516763acaf4d8d8b328cc758e6a5ab
Source dataset
uspto-grants-2016_09
Patent number
US09440949B2

Reaction notes

Loading…