Hydrochloric Acid → 7-(3-Difluoromethylphenyl)-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide

HRID 269987Notes

Reaction equation

HRID 269987 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][S:11]([C:14]1[C:15]2[CH:16]=[CH:17][N:18]=[CH:19][C:20]=2[CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([F:32])[F:31])[CH:25]=2)[CH:23]=1)(=[O:13])=[O:12])(C)(C)C.Cl>C(OCC)(=O)C.O1CCOCC1>[NH2:7][CH2:8][CH2:9][NH:10][S:11]([C:14]1[C:15]2[CH:16]=[CH:17][N:18]=[CH:19][C:20]=2[CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([F:32])[F:31])[CH:25]=2)[CH:23]=1)(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69327854{2-[7-(3-Difluoromethylpheny)-isoquinoline-5-sulfonylamino]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 112803467-(3-Difluoromethylphenyl)-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amideYield 95%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Suspend {2-[7-(3-difluoromethylpheny)-isoquinoline-5-sulfonylamino]-ethyl}-carbamic acid tert-butyl ester in ethyl acetate (11 mL), and add an excess of 4 M HCl in 1,4-dioxane. Stir overnight, filter the precipitate, wash with dichloromethane, and dry under vacuum to give the desired compound as a white solid (0.092 g, 95% yield): 1H NMR (CD3OD): δ9.92 (s, 1H), 9.10 (d, J=7.0 Hz, 1H), 9.04 (m, 2H), 8.80 (d, J=7.0 Hz, 1H), 8.09 (m, 2H), 7.74 (m, 2H), 6.94 (t, J=52.1 Hz, 1H), 3.25 (m, 2H), 3.15 (m, 2H). Load the product onto ion exchange resin and elute with 1N NH3 in methanol and concentrate to dryness to give the free base. (Used in example 97).

Workup

  1. filtrationfilter the precipitate
  2. washwash with dichloromethane
  3. customdry under vacuum

Sources & evidence

ORD record
ord-475d33fdef1f433eaf509d5d1b9b4628
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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