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

HRID 571708Notes

Reaction equation

HRID 571708 reaction equation
ClC1C=C(N[C@H](C2CC2)C(N[C@@H]2CCCN(C(OC(C)(C)C)=O)C2)=O)C=C(F)C=1.[Cl:30][C:31]1[CH:32]=[C:33]([NH:38][CH2:39][C:40]([NH:42][C@@H:43]2[CH2:48][CH2:47][CH2:46][N:45]([C:49](OC(C)(C)C)=O)[CH2:44]2)=[O:41])[CH:34]=[C:35]([Cl:37])[CH:36]=1.NC1C(C#N)=C(Cl)N=CN=1.ClC1[N:72]=[CH:71][N:70]=[C:69]([NH:73][CH:74]([CH3:76])[CH3:75])[CH:68]=1>>[Cl:37][C:35]1[CH:34]=[C:33]([NH:38][CH2:39][C:40]([NH:42][C@@H:43]2[CH2:48][CH2:47][CH2:46][N:45]([C:49]3[CH:68]=[C:69]([NH:73][CH:74]([CH3:76])[CH3:75])[N:70]=[CH:71][N:72]=3)[CH2:44]2)=[O:41])[CH:32]=[C:31]([Cl:30])[CH:36]=1

Participants

5

Reactant 4

HCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 217490304-Chloro-6-(isopropylamino)pyrimidineHCID 67066786(R)-tert-butyl 3-((R)-2-(3-chloro-5-fluorophenylamino)-2-cyclopropylacetamido)piperidine-1-carboxylateHCID 67969283(R)-tert-butyl 3-(2-(3,5-dichlorophenylamino)acetamido)piperidine-1-carboxylate

Product 1

HCID 67969246(R)-2-(3,5-dichlorophenylamino)-N-(1-(6-(isopropylamino)pyrimidin-4-yl)piperidin-3-yl)acetamide

Procedure

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.

Sources & evidence

ORD record
ord-c1ac5bc201ee49f1902e6f5d022598f5
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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