Pyridine → HCID 86652065, compound

HRID 1516414Notes

Reaction equation

HRID 1516414 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH2:30][CH2:31][OH:32])(=[NH:29])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1.N1C=CC=CC=1.[C:39](Cl)(=[O:41])[CH3:40]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH2:30][CH2:31][OH:32])(=[N:29][C:39](=[O:41])[CH3:40])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 25271234HCID 25271234, compound

Product 1

HCID 86652065HCID 86652065, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirring solution of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-(2-hydroxy ethyl)-sulfoximide (0.550 g, 0.00111 mol) in DCM(10 mL) was added pyridine (0.131 g, 0.001665 mol) at 5-10° C. under nitrogen atmosphere followed acetyl chloride (0.105 g, 0.00134 mol). Reaction mixture was stirred for 3 hr at 25-30° C. Subsequent work up and column purification (55% ethyl acetate in hexane and 100-200 mesh silica gel) gave 100 mg of desired product in 17% yield.

Workup

  1. customReaction mixture
  2. customSubsequent work up and column purification (55% ethyl acetate in hexane and 100-200 mesh silica gel)

Sources & evidence

ORD record
ord-aaba2c2c497145539994b82c62a02fe5
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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