Tert-Butylamine → HCID 47304733, compound

HRID 2219205Notes

Reaction equation

HRID 2219205 reaction equation
Cl.[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17].C(OCC)(=O)C>C(Cl)Cl>[C:16]([NH:20][S:12]([C:7]1[C:6]2[CH:5]=[CH:4][N:3]=[CH:2][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=[O:14])=[O:13])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8857Ethyl AcetateHCID 13116932Isoquinoline-5-sulfonyl chloride hydrochloride

Product 1

HCID 47304733HCID 47304733, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Powdered isoquinoline-5-sulfonyl chloride hydrochloride (1.00 g, 3.79 mmol) is added in small portions to a stirred solution of tert-butylamine (2.00 mL, 18.9 mmol) in CH2Cl2 (10 mL) at 0° C. under nitrogen. The resultant mixture is allowed to stir at ambient temperature for 1 hour. Ethyl acetate (50 mL) is added to the mixture and the mixture is washed with saturated aqueous NaHCO3 (20 mL). The organic layer is dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica (gradient 0-2% CH3OH in CH2Cl2) to give 857 mg (3.24 mmol, 86% yield) of the title compound as a white solid. ESIMS: m/z 265 (M+H)+. Analysis for C13H16N2O2S: calcd: C, 59.07; H, 6.10; N, 10.60; found: C, 59.21; H, 6.01; N, 10.67.

Workup

  1. washthe mixture is washed with saturated aqueous NaHCO3 (20 mL)
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is chromatographed on silica (gradient 0-2% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-c17ada61923c4cd4b3c9c89c7a0a4ed7
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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