4-Chloro-6-(ethylamino)pyrimidine → (R)-2-(3,5-dichlorophenylamino)-N-(1-(6-(ethylamino)pyrimidin-4-yl)piperidin-3-yl)acetamide

HRID 571709Notes

Reaction equation

HRID 571709 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][CH2:74][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][CH2:74][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 5884524-Chloro-6-(ethylamino)pyrimidineHCID 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 67969373(R)-2-(3,5-dichlorophenylamino)-N-(1-(6-(ethylamino)pyrimidin-4-yl)piperidin-3-yl)acetamide

Procedure

The title compound of Example 143 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-ethylpyrimidin-4-amine. 1H NMR (300 MHz, CD3OD) δ 8.08 (s, 1H), 6.63 (t, J=1.70 Hz, 1H), 6.48 (d, J=1.89 Hz, 2H), 5.70 (s, 1H), 3.89-4.03 (m, 2H), 3.74 (s, 2H), 3.55 (d, J=7.55 Hz, 2H), 1.91-2.03 (m, 1H), 1.76-1.87 (m, 2H), 1.65 (dt, J=4.20, 8.59 Hz, 1H), 1.26 (t, J=7.18 Hz, 3H). EIMS (m/z): calcd. for C19H24Cl2N6O (M+1H) 423. found 423.

Sources & evidence

ORD record
ord-a37c7630ab2c42bb85f452527ea4bb79
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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