Lithium Hydroxide → HCID 118366209, compound

HRID 59916Notes

Reaction equation

HRID 59916 reaction equation
[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].[NH2:26][CH2:27][C:28]1[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=1)[C:31]([O:33]C)=[O:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Li+].[OH-]>>[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:26][CH2:27][C:28]3[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=3)[C:31]([OH:33])=[O:32])=[O:18])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2]

Participants

5

Reactant 4

HCID 3939Lithium HydroxideHCID 2794826Methyl 3-(aminomethyl)benzoateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118366232(R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinic acid

Product 1

HCID 118366209HCID 118366209, compound

Procedure

(R)-3-((6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinamido)methyl)benzoic acid was prepared from (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinic acid and methyl 3-(aminomethyl)benzoate using Amidation Method 1 (HATU) and Ester Hydrolysis Method 1 (LiOH). 1H NMR (500 MHz, CD3OD) δ 8.84 (app t, 1H), 8.58 (d, 1H), 8.02 (s, 1H), 7.92 (dd, 2H), 7.58 (d, 1H), 7.44 (t, 1H), 7.01 (d, 1H), 6.92 (m, 2H), 6.87 (m, 1H), 6.73 (d, 1H), 4.60 (m, 2H), 4.37 (m, 1H), 4.05 (dd, 1H), 3.93 (m, 2H), 3.72 (m, 3H), 2.07 (m, 1H), 1.95 (m, 2H), 1.59 (m, 1H), 1.28 (t, 3H). MS (ES+) 476.3 (M+H).

Sources & evidence

ORD record
ord-9f9faf93068b47129ce233e034bb5f22
Source dataset
uspto-grants-2016_09
Patent number
US09440949B2

Reaction notes

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