1-(Bromomethyl)-2-chloro-4-(methylsulfonyl)benzene → 4-[5-Bromo-2-[[1-[(4-methylsulfonylphenyl)methyl]-4-piperidyl]amino]pyrimidin-4-yl]oxy-3,5-dimethyl-benzonitrile

HRID 1672501Notes

Reaction equation

HRID 1672501 reaction equation
[Br:1][C:2]1[C:3]([O:15][C:16]2[C:23]([CH3:24])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=2Cl)=[N:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1.Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][C:29]=1Cl.Br[CH2:40]C1C=CC(C(N)=O)=CC=1Cl.BrCC1C=CC(S(N)(=O)=O)=CC=1Cl>>[Br:1][C:2]1[C:3]([O:15][C:16]2[C:23]([CH3:24])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=2[CH3:40])=[N:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=3)[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 27610831-(Bromomethyl)-2-chloro-4-(methylsulfonyl)benzeneHCID 186290154-Bromomethyl-3-chloro-benzenesulfonamideHCID 215690484-Bromomethyl-3-chloro-benzamideHCID 673400854-[5-Bromo-2-(piperidin-4-ylamino)-pyrimidin-4-yloxy]-3-chloro-5-methyl-benzonitrile

Product 1

HCID 497981834-[5-Bromo-2-[[1-[(4-methylsulfonylphenyl)methyl]-4-piperidyl]amino]pyrimidin-4-yl]oxy-3,5-dimethyl-benzonitrile

Procedure

I-51, I-59 and I-60 were prepared analogously except 56 was replaced with 4-[5-bromo-2-(piperidin-4-ylamino)-pyrimidin-4-yloxy]-3-chloro-5-methyl-benzonitrile and 59 was replaced with 1-bromomethyl-2-chloro-4-methanesulfonyl-benzene, 4-bromomethyl-3-chloro-benzamide and 4-bromomethyl-3-chloro-benzenesulfonamide respectively.

Workup

  1. customI-51, I-59 and I-60 were prepared analogously except 56

Sources & evidence

ORD record
ord-fed9c4f67e35405fa9a8509e0069fcab
Source dataset
uspto-grants-2011_08
Patent number
US07998969B2

Reaction notes

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