Hydrochloric Acid → HCID 67329989, compound

HRID 1672361Notes

Reaction equation

HRID 1672361 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][S:10]([C:13]1[C:14]2[CH:15]=[CH:16][N:17]=[CH:18][C:19]=2[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH:22]=1)(=[O:12])=[O:11])(C)(C)C.[ClH:32]>CO.O1CCOCC1>[ClH:32].[ClH:32].[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:21]2[CH:22]=[C:13]([S:10]([CH2:9][CH2:8][NH2:7])(=[O:12])=[O:11])[C:14]3[CH:15]=[CH:16][N:17]=[CH:18][C:19]=3[CH:20]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67331428HCID 67331428, compound

Product 1

HCID 67329989HCID 67329989, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Treat a slurry of {2-[7-(4-methoxy-phenyl)-isoquinoline-5-sulfonyl]-ethyl}-carbamic acid tert-butyl ester (11.00 g, 24.85 mmol) in anhydrous MeOH (150 mL) with 4N HCl in dioxane (350 mL). Stir the resulting reaction mixture at room temperature overnight, then concentrate in vacuo to ½ volume and treat with excess EtOAc, causing a yellow solid to precipitate. Recover the resulting solid by vacuum filtration under an N2 atmosphere; wash with EtOAc and dry under vacuum (under an N2 atmosphere) to afford the title compound (10.23 g, 99% yield) as a yellow solid: MS (ES): m/z 343.0 (M++H).

Workup

  1. customthe resulting reaction mixture at room temperature overnight
  2. concentrationconcentrate in vacuo
  3. additiontreat with excess EtOAc
  4. customto precipitate
  5. customRecover the resulting solid
  6. filtrationby vacuum filtration under an N2 atmosphere
  7. washwash with EtOAc
  8. customdry under vacuum (under an N2 atmosphere)

Sources & evidence

ORD record
ord-f4418c86605645939d961814a49b43c0
Source dataset
uspto-grants-2011_08
Patent number
US07998977B2

Reaction notes

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