Water → HCID 10468517, compound

HRID 351109Notes

Reaction equation

HRID 351109 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[NH2:15][C:16]1[S:20][C:19]2[C:21]3[C:26]([CH2:27][C:18]=2[C:17]=1[C:28]([NH2:30])=[O:29])=[CH:25][CH:24]=[CH:23][CH:22]=3.O>ClCCl>[C:10]([OH:12])([C:9]([F:14])([F:13])[F:8])=[O:11].[NH:15]([C:16]1[S:20][C:19]2[C:21]3[C:26]([CH2:27][C:18]=2[C:17]=1[C:28]([NH2:30])=[O:29])=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:6]([NH2:5])=[O:7]

Participants

6

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 69370652HCID 69370652, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 10468517HCID 10468517, compoundYield 255.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chlorosulfonyl isocyanate (0.025 g, 0.17 mL) was added dropwise to a stirred solution of 2-amino-4H-indeno[1,2-b]thiophene-3-carboxylic acid amide trifluoroacetate (0.040 g, 0.17 mmol) in dry dichloromethane (2 mL). The resulting reaction mixture was stirred under nitrogen for 30 min. Water (0.5 mL) was then added to the reaction mixture and the reaction mixture was allowed to stir an additional 10 minutes before the solvent was removed under vacuo. The residue was then purified on Gilson preparative HPLC (YMC HPLC column 50×20 mm I.D., s-5 μm, 120 A; gradient elution, 0.1% TFA in acetonitrile: 0.1% aqueous TFA, 10:90 to 90:10, 10 min) to give title compound as brown solid (0.020 g, 0.435 mmol, 43.5% yield). ESMS m/z: 274 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringto stir an additional 10 minutes before the solvent
  3. customwas removed under vacuo
  4. customThe residue was then purified on Gilson preparative HPLC (YMC HPLC column 50×20 mm I.D
  5. washgradient elution, 0.1% TFA in acetonitrile

Sources & evidence

ORD record
ord-5377a88cacd040a2821f022d13cf49c2
Source dataset
uspto-grants-2007_02
Patent number
US07183311B2

Reaction notes

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