4-(Bromomethyl)benzoic acid → HCID 58614895, compound

HRID 922970Notes

Reaction equation

HRID 922970 reaction equation
ClC1C=CC(N)=CC=1C1C=CC=CN=1.BrCC1C=CC(C(O)=O)=CC=1.Br[CH2:27][C:28]1[CH:49]=[CH:48][C:31]([C:32]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)[CH:36]=2)=[O:33])=[CH:30][CH:29]=1.Cl.[CH3:51][N:52]([CH3:56])[CH2:53][CH2:54]S.ClC1C=CC(NC(=O)C2C=CC(CSCCN(C)C)=CC=2)=CC=1C1C=CC=CN=1.O[O:87][S:88]([O-:90])=O.[K+]>>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([NH:34][C:32](=[O:33])[C:31]2[CH:48]=[CH:49][C:28]([CH2:27][S:88]([CH2:54][CH2:53][N:52]([CH3:56])[CH3:51])(=[O:90])=[O:87])=[CH:29][CH:30]=2)=[CH:36][C:37]=1[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=1

Participants

7

Reactant 6

HCID 225994-(Bromomethyl)benzoic acidHCID 25798Captamine HydrochlorideHCID 23707502Potassium hydroxy sulfiteHCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 66877754HCID 66877754, compoundHCID 668781704-(Bromomethyl)-N-[4-chloro-3-(2-pyridinyl)phenyl]benzamide

Product 1

HCID 58614895HCID 58614895, compound

Procedure

500 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-(bromomethyl)benzoic acid via Procedure E. 170 mg of 4-(bromomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide was reacted with 2-(dimethylamino)ethanethiol hydrochloride via Procedure Q. 140 mg of crude N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((2-(dimethylamino)ethylthio)methyl)benzamide was reacted with oxone via Procedure R. The crude product was purified by reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((2-(dimethylamino)ethylsulfonyl)methyl)benzamide. MS (Q1) 458.3 (M)+.

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-bfb87fc584924bcbae7cbd012d422d29
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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