1-(Methanesulfonyl)piperidin-4-amine → [2-Amino-6-(1-methanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone

HRID 30137Notes

Reaction equation

HRID 30137 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[CH3:21][S:22]([N:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1)(=[O:24])=[O:23]>>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][CH:5]=[C:4]([NH:31][CH:28]2[CH2:29][CH2:30][N:25]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:26][CH2:27]2)[N:3]=1

Participants

3

Reactant 2

HCID 113558261-(Methanesulfonyl)piperidin-4-amineHCID 58590826(2-Amino-6-chloro-pyridin-3-yl)-(2,3-difluoro-6-methoxy-phenyl)-methanone

Product 1

HCID 11597358[2-Amino-6-(1-methanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone

Procedure

The title compound was prepared from (2-Amino-6-chloro-pyridin-3-yl)-(2,3-difluoro-6-methoxy-phenyl)-methanone (Example 39) and 1-methanesulfonyl-piperidin-4-ylamine (Step A. Example 6) using the procedure described in Step B. Example 6. HRMS, observed: 441.1407, Calcd for (M+H)+: 441.1403. Ki for cdk4=0.017 μM, cdk1=0.060 μM, cdk2=0.054 and IC50 for HCT116 cell line=2.6 μM.

Sources & evidence

ORD record
ord-6ba95a377bb14a658d85e0dcd2a5c19d
Source dataset
uspto-grants-2008_09
Patent number
US07423051B2

Reaction notes

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