6-chloro-N-methylpyrimidin-4-amine → (R)-2-(3,5-dichlorophenylamino)-N-(1-(6-(methylamino)pyrimidin-4-yl)piperidin-3-yl)acetamide

HRID 571710Notes

Reaction equation

HRID 571710 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][CH3:74])[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][CH3:74])[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 3094796-chloro-N-methylpyrimidin-4-amineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 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 67969427(R)-2-(3,5-dichlorophenylamino)-N-(1-(6-(methylamino)pyrimidin-4-yl)piperidin-3-yl)acetamide

Procedure

The title compound of Example 144 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-methylpyrimidin-4-amine. 1H NMR (300 MHz, CD3OD) δ 8.08 (s, 1H), 6.63 (s, 1H), 6.48 (d, J=1.51 Hz, 2H), 5.69 (s, 1H), 3.91 (dd, J=3.78, 7.55 Hz, 3H), 3.74 (s, 2H), 3.50-3.67 (m, 2H), 2.90 (s, 3H), 1.96 (dt, J=4.53, 9.06 Hz, 1H), 1.73-1.88 (m, 2H), 1.57-1.73 (m, 1H). EIMS (m/z): calcd. for C18H22Cl2N6O (M+1H) 409. found 409.

Sources & evidence

ORD record
ord-bf72b4dabe984ba6a1b7d408f9c4486f
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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