Hydrochloric Acid → HCID 178479395, compound

HRID 2289789Notes

Reaction equation

HRID 2289789 reaction equation
[ClH:1].C([O:6][C:7](=[O:31])[C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[S:13]([C:16]1[CH:25]=[C:24]2[C:19]([C:20]([Br:30])=[CH:21][N:22]=[C:23]2[NH:26][C:27]([NH2:29])=[NH:28])=[CH:18][CH:17]=1)(=[O:15])=[O:14])(C)(C)C.Cl>CCOC(C)=O>[ClH:1].[Br:30][C:20]1[C:19]2[C:24](=[CH:25][C:16]([S:13]([N:9]3[CH2:10][CH2:11][CH2:12][C@@H:8]3[C:7]([OH:31])=[O:6])(=[O:15])=[O:14])=[CH:17][CH:18]=2)[C:23]([NH:26][C:27]([NH2:29])=[NH:28])=[N:22][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451174HCID 178451174, compound

Product 1

HCID 178479395HCID 178479395, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Anal. Found: C, 41.96: H, 4.65; N, 12.65. Calc. for C19H24BrN5O4S.HCl.90.5H2O: C, 41.96:, 4.82; N, 12.88%. N-[(4-Bromo-1-guanidino-7-isoquinolinyl)sulphonyl]-D-proline tert-butyl ester hydrochloride (150 mg, 0.28 mmol) was treated with an ice-cold solution of HCl in EtOAc (20 ml), and the reaction allowed to warm to room temperature, and stirred for 4 h. The solution was concentrated in vacuo and the crude product purified by column chromatography upon silica gel using CH2Cl2 -MeOH-0.880 NH3 (90:10:1) as eluant. The product was treated with ethereal HCl, the resulting precipitate filtered, washed with Et2O and dried to afford N-[(4-bromo-1-guanidino-7-isoquinolinyl)sulphonyl]-D-proline hydrochloride (75 mg, 0.156 mmol) as a white powder.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe crude product purified by column chromatography upon silica gel
  3. additionThe product was treated with ethereal HCl
  4. filtrationthe resulting precipitate filtered
  5. washwashed with Et2O
  6. customdried

Sources & evidence

ORD record
ord-db497f018458486f8436348dd1bb87cd
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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