Lithium Hydroxide → HCID 118366238, compound

HRID 59923Notes

Reaction equation

HRID 59923 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[N:18]=[CH:17][C:16]([C:19](O)=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].Cl.[NH2:27][CH2:28][C:29]1[C:30]([O:40][CH3:41])=[C:31]([CH:37]=[CH:38][CH:39]=1)[C:32]([O:34]CC)=[O:33].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[N:18]=[CH:17][C:16]([C:19]([NH:27][CH2:28][C:29]3[C:30]([O:40][CH3:41])=[C:31]([CH:37]=[CH:38][CH:39]=3)[C:32]([OH:34])=[O:33])=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2]

Participants

5

Reactant 4

HCID 3939Lithium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118366163Ethyl 3-(aminomethyl)-2-methoxybenzoate hydrochlorideHCID 118366221(R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid

Product 1

HCID 118366238HCID 118366238, compound

Procedure

(R)-3-((2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)-2-methoxybenzoic acid was prepared from (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid and ethyl 3-(aminomethyl)-2-methoxybenzoate hydrochloride using Amidation Method 1 (HATU) and Ester Hydrolysis Method 1 (LiOH). 1H NMR (300 MHz, DMSO-d6) δ 12.6 (s, 1H), 8.78 (s, 3H), 7.88 (d, 1H), 7.78 (s, 1H), 7.10 (d, 1H), 7.05 (d, 1H), 6.90 (m, 3H), 4.45 (d, 2H), 4.36 (m, 1H), 4.18 (d, 1H), 3.90 (m, 8H), 2.05 (m, 1H), 1.87 (m, 2H), 1.52 (m, 1H), 1.21 (t, 3H). MS (ES+) 507.0 (M+H).

Sources & evidence

ORD record
ord-6a4f8987cb714f5ca152ea1471478fa2
Source dataset
uspto-grants-2016_09
Patent number
US09440949B2

Reaction notes

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