HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Amino-6-chloropyrimidine-5-carbonitrile → (R)-2-(3,5-dichlorophenylamino)-N-(1-(6-(isopropylamino)pyrimidin-4-yl)piperidin-3-yl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Amino-6-chloropyrimidine-5-carbonitrile | HCID 12278262 | — |
| Reactant | 4-Chloro-6-(isopropylamino)pyrimidine | HCID 21749030 | — |
| Reactant | (R)-tert-butyl 3-((R)-2-(3-chloro-5-fluorophenylamino)-2-cyclopropylacetamido)piperidine-1-carboxylate | HCID 67066786 | — |
| Reactant | (R)-tert-butyl 3-(2-(3,5-dichlorophenylamino)acetamido)piperidine-1-carboxylate | HCID 67969283 | — |
| Product | (R)-2-(3,5-dichlorophenylamino)-N-(1-(6-(isopropylamino)pyrimidin-4-yl)piperidin-3-yl)acetamide | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09029359B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-c1ac5bc201ee49f1902e6f5d022598f5 |
| Source note | uspto-grants-2015_05 |