N-(6-chloropyrimidin-4-yl)acetamide → HCID 67066774, compound

HRID 571707Notes

Reaction equation

HRID 571707 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][C:74](=[O:76])[CH3:75])[CH:68]=1>>[C:74]([NH:73][C:69]1[N:70]=[CH:71][N:72]=[C:49]([N:45]2[CH2:46][CH2:47][CH2:48][C@@H:43]([NH:42][C:40](=[O:41])[CH2:39][NH:38][C:33]3[CH:34]=[C:35]([Cl:37])[CH:36]=[C:31]([Cl:30])[CH:32]=3)[CH2:44]2)[CH:68]=1)(=[O:76])[CH3:75]

Participants

5

Reactant 4

HCID 539477N-(6-chloropyrimidin-4-yl)acetamideHCID 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 67066774HCID 67066774, compound

Procedure

The title compound of Example 141 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 N-(6-chloropyrimidin-4-yl)acetamide. 1H NMR (400 MHz, DMSO-d6) δ 10.32 (s, 1H), 8.17 (s, 1H), 7.96 (d, J=7.78 Hz, 1H), 6.56 (t, J=1.88 Hz, 1H), 6.47 (d, J=1.76 Hz, 2H), 4.02 (br. s., 1H), 3.79 (br. s., 1H), 3.61 (d, J=9.29 Hz, 3H), 2.84-3.17 (m, 2H), 2.00 (s, 3H), 1.75 (br. s., 2H), 1.33-1.57 (m, 2H). EIMS (m/z): calcd. for C19H22Cl2N6O2 (M+1H) 437. found 437.

Sources & evidence

ORD record
ord-c673101529ae4ca8b26d8c7592691363
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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