Acetic Acid → HCID 23152565, compound

HRID 1012309Notes

Reaction equation

HRID 1012309 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[NH2:25])[NH:15]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].C(O)(=O)C.[Cl:41][CH2:42][C:43](Cl)=[O:44]>O1CCCC1>[C:1]([NH:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[NH:25][C:43](=[O:44])[CH2:42][Cl:41])[NH:15]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 23152927HCID 23152927, compound

Product 1

HCID 23152565HCID 23152565, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-tert-butyl-2-(2-amino-4-methylphenyl)-3-cyclohexyl-1H-indole-6-sulfonamide (2.14 g, 4.86 mmol), sodium acetate (472 mg, 5.75 mmol) and acetic acid (0.33 ml, 5.76 mmol) in tetrahydrofuran (20 ml) was added dropwise chloroacetyl chloride (0.45 ml, 5.64 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. the reaction mixture was concentrated under reduced pressure, and water was added to the residue. The precipitated solid was collected by filtration and dried in vacuo. A suspension of the obtained solid in diethyl ether was stirred at room temperature for 1 hr. The solid was collected by filtration and dried in vacuo to give N-tert-butyl-2-[2-(chloroacetylamino)-4-methylphenyl]-3-cyclohexyl-1H-indole-6-sulfonamide (2.22 g, yield 89.9%). The obtained crude product was used for Step 10 without further purification.

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure, and water
  3. additionwas added to the residue
  4. filtrationThe precipitated solid was collected by filtration
  5. customdried in vacuo
  6. additionA suspension of the obtained solid in diethyl ether
  7. stirringwas stirred at room temperature for 1 hr
  8. filtrationThe solid was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-ef7f35ab479d401f9475a9f9f5571acb
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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