Hydrochloric Acid → HCID 178479779, compound

HRID 2219232Notes

Reaction equation

HRID 2219232 reaction equation
Cl.[F:2][C:3]([F:32])([F:31])[C:4]1[CH:30]=[CH:29][CH:28]=[CH:27][C:5]=1[O:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]2[CH:18]=[CH:19][N:20]=[C:21]([Cl:26])[C:22]=2[CH:23]=[CH:24][CH:25]=1)(=[O:15])=[O:14].C1C[O:36]CC1>>[ClH:26].[F:2][C:3]([F:32])([F:31])[C:4]1[CH:30]=[CH:29][CH:28]=[CH:27][C:5]=1[O:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]2[CH:18]=[CH:19][N:20]=[C:21]([OH:36])[C:22]=2[CH:23]=[CH:24][CH:25]=1)(=[O:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 866109341-Chloro-isoquinoline-5-sulfonic acid {2-[2-(2-trifluoromethyl-phenoxy)-ethylamino]-ethyl}-amide

Product 1

HCID 178479779HCID 178479779, compoundYield 33%

Procedure

A 0.6 mL 5N HCl solution is added to a stirred solution of 1-chloro-isoquinoline-5-sulfonic acid {2-[2-(2-trifluoromethyl-phenoxy)-ethylamino]-ethyl}-amide (70 mg, 0.15 mmol) in THF (1 mL) at ambient temperature under nitrogen. The resultant mixture is heated at 65° C. for 16 hours. At ambient temperature, the mixture is concentrated. The crude product is dissolved in a small amount of MeOH/CH2Cl2 before it is treated with Et2O to form a white suspension. After filtration and vacuum drying, 24 mg (0.49 mmol, 33% yield) of the title compound is obtained as a white powder. ESIMS: m/z 456 (M+H)+.

Workup

  1. concentrationAt ambient temperature, the mixture is concentrated
  2. dissolutionThe crude product is dissolved in a small amount of MeOH/CH2Cl2 before it
  3. additionis treated with Et2O
  4. customto form a white suspension
  5. filtrationAfter filtration and vacuum
  6. customdrying

Sources & evidence

ORD record
ord-9caefb1e334b49619c2b973d79fe34ae
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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