Acetaldehyde → 3-Amino-5-chloro-3-(2-chlorophenyl)-1-[2-(ethylamino)-4-methoxybenzenesulfonyl]-1,3-dihydroindol-2-one

HRID 965575Notes

Reaction equation

HRID 965575 reaction equation
[CH:1](=O)[CH3:2].C([BH3-])#N.[Na+].[NH2:8][C:9]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[Cl:38])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[N:11]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[NH2:30])(=[O:21])=[O:20])[C:10]1=[O:31].C(=O)([O-])[O-].[K+].[K+]>CO.Cl.CC(O)=O>[NH2:8][C:9]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[Cl:38])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[N:11]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[NH:30][CH2:1][CH3:2])(=[O:21])=[O:20])[C:10]1=[O:31]

Participants

8

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 190764183-Amino-1-(2-amino-4-methoxybenzenesulfonyl)-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one

Product 1

HCID 190764703-Amino-5-chloro-3-(2-chlorophenyl)-1-[2-(ethylamino)-4-methoxybenzenesulfonyl]-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

2.6 ml of AcOH and then 0.09 ml of acetaldehyde and 0.038 g of sodium cyanoborohydride are added at RT to a solution of 0.830 g of the compound obtained in EXAMPLE 106 in 22 ml of MeOH. After stirring for 4 hours at RT, 2 drops of concentrated HCl are added and the reaction mixture is then neutralized by the addition of a 5% solution of potassium carbonate. The solvent is concentrated under vacuum, the residue is extracted with AcOEt, the organic phase is washed with water and with a saturated solution of sodium chloride and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/hexane mixture (80/20; v/v) and then DCM as the eluent to give 0.396 g of the expected product after crystallization from a DCM/iso ether mixture. M.p.=192°-196° C.

Workup

  1. concentrationThe solvent is concentrated under vacuum
  2. extractionthe residue is extracted with AcOEt
  3. washthe organic phase is washed with water and with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica using a DCM/hexane mixture (80/20; v/v)

Sources & evidence

ORD record
ord-1b85fc1fad9347989c585b151070f943
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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