Lithium Hydroxide → HCID 118366274, compound

HRID 59917Notes

Reaction equation

HRID 59917 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][CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([C:35]([O:37]C)=[O:36])[CH:30]=1.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][CH2:28][C:29]3[CH:34]=[CH:33][N:32]=[C:31]([C:35]([OH:37])=[O:36])[CH:30]=3)=[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 53418010HCID 53418010, compoundHCID 118366159HCID 118366159, compound

Product 1

HCID 118366274HCID 118366274, compound

Procedure

(R)-4-((6-(3-(2-ethoxyphenoxy)piperidin-1-yl)-5-fluoronicotinamido)methyl)picolinic acid was prepared from (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)-5-fluoronicotinic acid and methyl 4-(aminomethyl)picolinate using Amidation Method 2 (EDCl) and Ester Hydrolysis Method 1 (LiOH). 1H NMR (500 MHz, CDCl3) δ 8.57 (d, 1H), 8.42 (s, 1H), 8.16 (s, 1H), 7.67 (dd, 1H), 7.57 (d, 1H), 7.03 (dd, 1H), 6.95 (m, 1H), 6.88 (m, 2H), 6.78 (br s, 1H), 4.74 (d, 2H), 4.34 (m, 1H), 4.29 (m, 1H), 4.03 (m, 2H), 3.93 (m, 1H), 3.49 (m, 1H), 3.43 (m, 1H), 2.17 (m, 1H), 2.01 (m, 1H), 1.89 (m, 1H), 1.64 (m, 1H), 1.40 (t, 3H). MS (ES+) 495.2 (M+H).

Sources & evidence

ORD record
ord-963c1352dc1945788bc37c5013cee986
Source dataset
uspto-grants-2016_09
Patent number
US09440949B2

Reaction notes

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