Lithium Hydroxide → US10188653, Example 11

Participants

Role	Name	HCID	Charge
Reactant	Lithium Hydroxide	HCID 3939	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	Methyl 3-(aminomethyl)-4-methoxybenzoate hydrochloride	HCID 118366175	—
Reactant	(R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid	HCID 118366221	—
Product	US10188653, Example 11	HCID 118366191	—

Reaction Steps

(R)-3-((2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)-4-methoxybenzoic acid was prepared from (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid and methyl 3-(aminomethyl)-4-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 (app s, 3H), 7.89 (dd, 1H), 7.76 (m, 1H), 7.10 (d, 1H), 7.05 (d, 1H), 6.89 (m, 3H), 4.45 (d, 2H), 4.38 (m, 1H), 4.18 (d, 1H), 3.91 (m, 8H), 2.05 (m, 1H), 1.88 (m, 2H), 1.52 (m, 1H), 1.21 (t, 3H). MS (ES+) 507.1 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09440949B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-265b428a994d405d914df47f87ff83bc
Source note	uspto-grants-2016_09