Dichloromethane → HCID 21962365, compound

HRID 1008644Notes

Reaction equation

HRID 1008644 reaction equation
Cl[C:2]1C=CC=C[C:3]=1CS(Cl)(=O)=O.[CH:13]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=2)[C:28]([CH2:36][CH2:37][O:38][C:39]2[CH:47]=[CH:46][C:42]([C:43]([OH:45])=[O:44])=[C:41]([F:48])[CH:40]=2)=[C:27]1[CH2:49][CH2:50][NH:51][S:52]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1Cl)(=[O:54])=[O:53])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].[CH2:68]([Cl:70])Cl>O>[CH:13]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=2)[C:28]([CH2:36][CH2:37][O:38][C:39]2[CH:47]=[CH:46][C:42]([C:43]([O:45][CH2:2][CH3:3])=[O:44])=[C:41]([F:48])[CH:40]=2)=[C:27]1[CH2:49][CH2:50][NH:51][S:52]([CH2:55][C:60]1[CH:59]=[CH:58][CH:57]=[CH:56][C:68]=1[Cl:70])(=[O:53])=[O:54])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2757801(2-Chlorophenyl)methanesulfonyl chlorideHCID 21962279HCID 21962279, compound

Product 1

HCID 21962365HCID 21962365, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[(2-chlorophenyl)methyl]sulfonyl chloride (0.14 g, 0.6 mmol) was added to a mixture of ethyl 4-{2-[2-(2-Aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethoxy}-2-fluoro-benzoate (Step 6, Example 190, 0.12 g, 0.2 mmol) and K2CO3 (0.11 g, 0.8 mmol) in CH2Cl2 (2 mL) and water (1 mL) with stirring. After 2 hour at room temperature, the mixture was extracted with CH2Cl2 (10 mL) and the extract was washed with 0.5 N NaOH, and brine and dried over sodium sulfate. The CH2Cl2 solution was filtered through silica gel and the filtrate was evaporated. The resulting residue was triturated with a mixture of ether and hexanes to give 0.07 g of ethyl 4-{2-[1-benzhydryl-5-chloro-2-(2-{[(2-chlorobenzyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]ethoxy}-2-fluorobenzoate as a white solid.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (10 mL)
  2. washthe extract was washed with 0.5 N NaOH, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe CH2Cl2 solution was filtered through silica gel
  5. customthe filtrate was evaporated
  6. customThe resulting residue was triturated with a mixture of ether and hexanes

Sources & evidence

ORD record
ord-001ef562b61645b898d543ac9301ffa6
Source dataset
uspto-grants-2004_09
Patent number
US06797708B2

Reaction notes

Loading…