1-(Methanesulfonyl)piperidin-4-amine → [2-Amino-6-(1-methanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

HRID 30120Notes

Reaction equation

HRID 30120 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[CH3:20][S:21]([N:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1)(=[O:23])=[O:22]>>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][CH:5]=[C:4]([NH:30][CH:27]2[CH2:28][CH2:29][N:24]([S:21]([CH3:20])(=[O:23])=[O:22])[CH2:25][CH2:26]2)[N:3]=1

Participants

3

Reactant 2

HCID 113558261-(Methanesulfonyl)piperidin-4-amineHCID 58590829(2-Amino-6-chloro-pyridin-3-yl)-(5-fluoro-2-methoxy-phenyl)-methanone

Product 1

HCID 11502705[2-Amino-6-(1-methanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

Procedure

The title compound was prepared from (2-amino-6-chloropyridin-3-yl)-(5-fluoro-2-methoxyphenyl)methanone (Example 19) and 1-methanesulfonylpiperidin-4-ylamine (Step A. Example 6) using the procedure described in Step B. Example 6. HRMS, observed: 423.1502, Calcd for (M+H)+: 423.1497. Ki for cdk4=0.040 μM, cdk2=0.098 μM, and IC50 for HCT116 cell line=9 μM.

Sources & evidence

ORD record
ord-4b8fa3e0c1a6437aa0ab2ff7ae7d41f7
Source dataset
uspto-grants-2008_09
Patent number
US07423051B2

Reaction notes

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