Dichloromethane → HCID 23114668, compound

HRID 2080456Notes

Reaction equation

HRID 2080456 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[C:6]([CH:16]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])=[CH:7][C:8]([N:11]([CH3:15])[CH2:12][CH2:13][OH:14])=[N:9][CH:10]=1.[CH2:35]([N:37]=[C:38]=[O:39])[CH3:36]>N1C=CC=CC=1>[CH2:35]([NH:37][C:38](=[O:39])[O:14][CH2:13][CH2:12][N:11]([C:8]1[CH:7]=[C:6]([CH:16]([S:25]([C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)(=[O:27])=[O:26])[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[C:5]([Cl:4])=[CH:10][N:9]=1)[CH3:15])[CH3:36]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8022Ethyl isocyanateHCID 23114548HCID 23114548, compound

Product 1

HCID 23114668HCID 23114668, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a methylene chloride (1.0 ml) solution of 2-[[5-chloro-4-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridin-2-yl](methyl)amino]ethanol (73 mg, 0.15 mmol) was added pyridine (0.5 ml), followed by further addition of ethyl isocyanate (100 μl). The resulting mixture was stirred for 19 hours. After the reaction mixture was concentrated under reduced pressure, the residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to yield the title compound (65 mg, 74%) as an oil.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. customwas purified by silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-657f28a51257476b9bee2be4eafa24a2
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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