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

HRID 571711Notes

Reaction equation

HRID 571711 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.[NH2:56][C:57]1[C:62](C#N)=C(Cl)[N:60]=[CH:59][N:58]=1.ClC1N=CN=C(N)C=1>>[NH2:56][C:57]1[N:58]=[CH:59][N:60]=[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:62]=1

Participants

5

Reactant 4

HCID 2380124-Amino-6-chloropyrimidineHCID 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 67969299(R)-N-(1-(6-aminopyrimidin-4-yl)piperidin-3-yl)-2-(3,5-dichlorophenylamino)acetamide

Procedure

The title compound of Example 145 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-chloropyrimidin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ 8.18 (s, 1H), 8.00 (d, J=7.28 Hz, 1H), 7.50 (br. s., 2H), 6.54-6.70 (m, 1H), 6.47 (d, J=1.76 Hz, 3H), 3.98 (br. s., 1H), 3.84 (br. s., 1H), 3.55-3.71 (m, 6H), 3.06 (dd, J=8.91, 12.93 Hz, 2H), 1.76 (br. s., 3H), 1.38-1.60 (m, 3H). EIMS (m/z): calcd. for C17H20Cl2N6O (M+1H) 395. found 395.

Sources & evidence

ORD record
ord-1c4f08722b5d4add8dbdbabe41415ece
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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