Methanol → HCID 10413996, compound

HRID 33598Notes

Reaction equation

HRID 33598 reaction equation
[CH3:1][OH:2].Cl[S:4]([N:7]=[C:8]=[O:9])(=[O:6])=[O:5].[NH2:10][C:11]1[C:12]([CH3:36])=[C:13]2[C:17](=[C:18]([NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C:19]=1[CH3:20])[N:16]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:15][CH2:14]2>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:8]([NH:7][S:4]([NH:10][C:11]1[C:12]([CH3:36])=[C:13]2[C:17](=[C:18]([NH:21][C:22](=[O:27])[C:23]([CH3:25])([CH3:26])[CH3:24])[C:19]=1[CH3:20])[N:16]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:15][CH2:14]2)(=[O:6])=[O:5])=[O:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 70918Chlorosulfonyl isocyanateHCID 23075425N-(5-Amino-4,6-dimethyl-1-octylindolin-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 10413996HCID 10413996, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Methanol (0.13 mL) was added to methylene chloride (2.6 mL) and chlorosulfonyl isocyanate (0.29 mL) was added at −20° C. The mixture was stirred at −20° C. to 10° C. for 20 min. N-(5-Amino-4,6-dimethyl-1-octylindolin-7-yl)-2,2-dimethylpropanamide (612 mg) and triethylamine (0.46 mL) were added to the reaction mixture and the mixture was further stirred at −9° C. for 30 min. Methylene chloride was added to the reaction mixture, and the mixture was washed successively with 10% aqueous citric acid, saturated aqueous sodium hydrogencarbonate and saturated brine and dried over sodium sulfate. Methylene chloride was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as crystals. (601 mg).

Workup

  1. additionwas added at −20° C
  2. stirringthe mixture was further stirred at −9° C. for 30 min
  3. washthe mixture was washed successively with 10% aqueous citric acid, saturated aqueous sodium hydrogencarbonate and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customMethylene chloride was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f87b85ae63044e2580b8bd74139cf8b7
Source dataset
uspto-grants-2008_09
Patent number
US07429612B2

Reaction notes

Loading…