Hydrochloric Acid → 1000210-63-8

HRID 1672370Notes

Reaction equation

HRID 1672370 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([C:7]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2)(=[O:6])=[O:5].[ClH:24].C([Cl:28])(=O)C.C(OCC)(=O)C>CO>[ClH:28].[ClH:24].[NH2:1][CH2:2][CH2:3][S:4]([C:7]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2)(=[O:5])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 236358031000210-64-92×

Product 1

HCID 236584011000210-63-8Yield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent5×

Procedure

Slurry 4-[5-(2-Amino-ethanesulfonyl)-isoquinolin-7-yl]-phenol (16.57 g, 50.45 mmol) in methanol (500 mL). Separately, prepare a solution of HCl in methanol by adding acetyl chloride (12.60 mL, 177.05 mmol) to methanol (165 mL). Add the solution of HCl in methanol dropwise at room temperature over 30 min to the slurry of 4-[5-(2-Amino-ethanesulfonyl)-isoquinolin-7-yl]-phenol in methanol. Stir for 30 min, then add ethyl acetate (600 mL) dropwise over 1 hour. Stir for 30 min, then filter the solids and wash with ethyl acetate (2×100 mL). Dry solids in vacuo at 50° C., then further dry in vacuo at room temperature with slow administration of nitrogen to afford the title compound (18.3 g, 90%). Mass spectrum (LCMS) m/z=329.0 (M+H+).

Workup

  1. stirringStir for 30 min
  2. filtrationfilter the solids
  3. washwash with ethyl acetate (2×100 mL)
  4. customDry solids in vacuo at 50° C.
  5. customfurther dry in vacuo at room temperature with slow administration of nitrogen

Sources & evidence

ORD record
ord-8ad65a14ecf740f09783b658308b0d1b
Source dataset
uspto-grants-2011_08
Patent number
US07998977B2

Reaction notes

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