4-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-one → (R)-2-(3,5-dichlorophenylamino)-N-(1-(6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-yl)acetamide

HRID 571712Notes

Reaction equation

HRID 571712 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[C:68]2[CH2:75][C:74](=[O:76])[NH:73][C:69]=2[N:70]=[CH:71][N:72]=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[C:68]4[CH2:75][C:74](=[O:76])[NH:73][C:69]=4[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 120958704-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-oneHCID 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 67969384(R)-2-(3,5-dichlorophenylamino)-N-(1-(6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-yl)acetamide

Procedure

The title compound of Example 146 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 4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one. 1H NMR (300 MHz, DMSO-d6) δ 10.99 (s, 1H), 8.17 (s, 1H), 8.03 (d, J=7.18 Hz, 1H), 6.62 (t, J=1.70 Hz, 1H), 6.54 (d, J=1.89 Hz, 2H), 4.13 (d, J=12.46 Hz, 3H), 3.69 (dd, J=11.33, 15.86 Hz, 10H), 2.84-3.22 (m, 2H), 1.82 (d, J=3.40 Hz, 1H), 1.66-1.76 (m, 1H), 1.43-1.63 (m, 2H). EIMS (m/z): calcd. for C19H20Cl2N6O (M+1H) 435. found 435.

Sources & evidence

ORD record
ord-5682d77414694bd6bd8f964bb52b9814
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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