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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 571711Generated: November 2, 2026

4-Amino-6-chloropyrimidine → (R)-N-(1-(6-aminopyrimidin-4-yl)piperidin-3-yl)-2-(3,5-dichlorophenylamino)acetamide

https://huagongshe.com/reaction/571711

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Amino-6-chloropyrimidineHCID 238012—
Reactant4-Amino-6-chloropyrimidine-5-carbonitrileHCID 12278262—
Reactant(R)-tert-butyl 3-((R)-2-(3-chloro-5-fluorophenylamino)-2-cyclopropylacetamido)piperidine-1-carboxylateHCID 67066786—
Reactant(R)-tert-butyl 3-(2-(3,5-dichlorophenylamino)acetamido)piperidine-1-carboxylateHCID 67969283—
Product(R)-N-(1-(6-aminopyrimidin-4-yl)piperidin-3-yl)-2-(3,5-dichlorophenylamino)acetamideHCID 67969299—

Reaction Steps

The title compound of Example 145 was prepared in similar manner as described in Example 134 except the key intermediate (R)-tert-butyl 3-((R)-2-(3-chloro-5-fluorophenylamino)-2-cyclopropylacetamido)piperidine-1-carboxylate was replaced with (R)-tert-butyl 3-(2-(3,5-dichlorophenylamino)acetamido)piperidine-1-carboxylate and the 4-amino-6-chloropyrimidine-5-carbonitrile was substituted for 6-chloropyrimidin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ 8.18 (s, 1H), 8.00 (d, J=7.28 Hz, 1H), 7.50 (br. s., 2H), 6.54-6.70 (m, 1H), 6.47 (d, J=1.76 Hz, 3H), 3.98 (br. s., 1H), 3.84 (br. s., 1H), 3.55-3.71 (m, 6H), 3.06 (dd, J=8.91, 12.93 Hz, 2H), 1.76 (br. s., 3H), 1.38-1.60 (m, 3H). EIMS (m/z): calcd. for C17H20Cl2N6O (M+1H) 395. found 395.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09029359B2
Source datasetuspto-grants-2015_05
ORD IDord-1c4f08722b5d4add8dbdbabe41415ece
Source noteuspto-grants-2015_05