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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 571708Generated: October 31, 2026

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

https://huagongshe.com/reaction/571708

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Amino-6-chloropyrimidine-5-carbonitrileHCID 12278262—
Reactant4-Chloro-6-(isopropylamino)pyrimidineHCID 21749030—
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)-2-(3,5-dichlorophenylamino)-N-(1-(6-(isopropylamino)pyrimidin-4-yl)piperidin-3-yl)acetamideHCID 67969246—

Reaction Steps

The title compound of Example 142 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-chloro-N-isopropylpyrimidin-4-amine. 1H NMR (300 MHz, CD3OD) δ 8.08 (s, 1H), 6.63 (t, J=1.89 Hz, 2H), 6.48 (d, J=1.89 Hz, 3H), 5.72 (s, 1H), 3.78-4.05 (m, 5H), 3.42-3.60 (m, 3H), 1.90-2.08 (m, 2H), 1.80 (td, J=3.59, 8.97 Hz, 3H), 1.65 (td, J=3.21, 8.03 Hz, 2H), 1.13-1.39 (m, 13H). EIMS (m/z): calcd. for C20H26O2N6O (M+1H) 437. found 437.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09029359B2
Source datasetuspto-grants-2015_05
ORD IDord-c1ac5bc201ee49f1902e6f5d022598f5
Source noteuspto-grants-2015_05