Dichloromethane → HCID 23114606, compound

HRID 2080411Notes

Reaction equation

HRID 2080411 reaction equation
Cl[CH2:2][Cl:3].ClC1C=CC(S([CH:14]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[C:15]2[N:20]=[CH:19][C:18](CN)=[CH:17][CH:16]=2)(=O)=O)=CC=1.C[N:32]1[CH2:37]COCC1.[C:38]([C:40]1[CH:41]=[C:42]([S:46](Cl)(=[O:48])=[O:47])[CH:43]=[CH:44][CH:45]=1)#[N:39]>CCCCCC>[Cl:3][C:2]1[CH:44]=[CH:43][C:42]([S:46]([C:19]2[N:20]=[C:15]([CH2:14][C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=3[F:30])[C:16]([CH2:37][NH:32][S:46]([C:42]3[CH:43]=[CH:44][CH:45]=[C:40]([C:38]#[N:39])[CH:41]=3)(=[O:48])=[O:47])=[CH:17][CH:18]=2)(=[O:48])=[O:47])=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 23114559[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine

Product 1

HCID 23114606HCID 23114606, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a dichloromethane (0.5 ml) solution of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine (28 mg, 0.068 mmol) obtained in Example 63 were added N-methylmorpholine (0.015 ml, 0.14 mmol) and 3-cyanobenzenesulfonyl chloride (22 mg, 0.10 mmol) sequentially at 0° C. The resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was washed with 1N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=7:3 eluate was concentrated under reduced pressure. The solid thus obtained was washed with hexane and collected by filtration to give the title compound (23 mg, 0.040 mmol, 59%) as a white solid.

Workup

  1. washThe reaction mixture was washed with 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=7:3 eluate was concentrated under reduced pressure
  7. customThe solid thus obtained
  8. washwas washed with hexane
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4ea4565ea7e54fa6b228178560c72173
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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