4-Amino-6-chloropyrimidine-5-carbonitrile → HCID 67066808, compound

HRID 571706Notes

Reaction equation

HRID 571706 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.[Cl:66][C:67]1[C:68]([NH2:74])=[N:69][CH:70]=[N:71]C=1Cl>>[NH2:74][C:68]1[N:69]=[CH:70][N:71]=[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)[C:67]=1[Cl:66]

Participants

5

Reactant 4

HCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 670667861-Piperidinecarboxylic acid, 3-[[(2R)-2-[(3-chloro-5-fluorophenyl)amino]-2-cyclopropylacetyl]amino]-, 1,1-dimethylethyl ester, (3R)-HCID 67969283HCID 67969283, compound

Product 1

HCID 67066808HCID 67066808, compound

Procedure

The title compound of Example 140 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 5,6-dichloropyrimidin-4-amine. 1H NMR (300 MHz, CD3OD) δ 7.91 (s, 1H), 6.51-6.63 (m, 1H), 6.34 (d, J=1.51 Hz, 2H), 3.93-4.10 (m, 1H), 3.47-3.57 (m, 3H), 3.20-3.31 (m, 2H), 2.76-3.01 (m, 1H), 1.72-1.85 (m, 2H), 1.54-1.67 (m, 2H). EIMS (m/z): calcd. for C17H19Cl3N6O (M+1H) 431. found 431.

Sources & evidence

ORD record
ord-0767551acabe47769bd3741fb56ef33f
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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