(R)-5-Bromo-3-(5-(2,4-dimethylpiperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one → (S)-5-Bromo-3-(5-(2,4-dimethylpiperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one

HRID 1026425Notes

Reaction equation

HRID 1026425 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][C@H:18]3[CH3:24])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.BrC1C=C(NC2C=CC(N3CCNC[C@@H]3C)=CN=2)C(=O)N(C)C=1>>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][C@@H:18]3[CH3:24])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 2

HCID 86683720(R)-5-Bromo-3-(5-(2,4-dimethylpiperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-oneHCID 86683723(S)-5-bromo-1-methyl-3-(5-(2-methylpiperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one

Product 1

HCID 86683722(S)-5-Bromo-3-(5-(2,4-dimethylpiperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-oneYield 75%

Procedure

Following the procedures as described for compound 109e, (S)-5-bromo-1-methyl-3-(5-(2-methylpiperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one (377 mg, 1 mmol) was methylated by reductive formylation to give 110a as a white solid (294 mg, 75%). LCMS: [M+H]+ 393. See FIG. 10.

Sources & evidence

ORD record
ord-249d7b25f12c466cbc625d472c6e9c49
Source dataset
uspto-grants-2014_05
Patent number
US08729072B2

Reaction notes

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