Hydrochloric Acid → HCID 86610758, compound

HRID 270002Notes

Reaction equation

HRID 270002 reaction equation
C(OC(=O)[N:7]([CH2:20][CH2:21][NH:22][S:23]([C:26]1[C:27]2[CH:28]=[CH:29][N:30]=[CH:31][C:32]=2[CH:33]=[C:34]([C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=2)[CH:35]=1)(=[O:25])=[O:24])[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)(C)(C)C.[ClH:44]>C(Cl)Cl.CO>[ClH:44].[ClH:44].[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][CH2:8][NH:7][CH2:20][CH2:21][NH:22][S:23]([C:26]2[C:27]3[CH:28]=[CH:29][N:30]=[CH:31][C:32]=3[CH:33]=[C:34]([C:36]3[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=3)[CH:35]=2)(=[O:25])=[O:24])=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69313528HCID 69313528, compound

Product 1

HCID 86610758HCID 86610758, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To {2-[7-(4-hydroxy-phenyl)-isoquinoline-5-sulfonylamino]-ethyl}-[3-(4-nitro-phenyl)-propyl]-carbamic acid tert-butyl ester, (0.090 g, 0.148 mmol) in 6 ml (1:1) CH2Cl2/MeOH bubble HCl (g) for several minutes, then stir for 1 h and filter to give 0.0859 g of 7-(4-hydroxy-phenyl)-isoquinoline-5-sulfonic acid {2-[3-(4-nitro-phenyl)-propylamino]-ethyl}-amide dihydrochloric acid in 100% yield. ES Positive Ion MS [M+H]+ ion observed: m/z 507. 1H-NMR (DMSO-d6) δ9.62 (s, 1H), 8.93 (br s, 2H), 8.75 (s, 1H), 8.69-8.71 (m, 2H), 8.61 (s, 1H), 8.52 (d, J=6.2 Hz, 1H), 8.15 (d, J=8.8 Hz, 2H), 7.75 (d, J=8.8 Hz, 2H), 7.48 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 3.10-3.15 (br m, 2H), 2.90-3.00 (br s, 2H), 2.87 (br s, 2H), 2.75 (t, J=7.5 Hz; 2H), 1.87-1.90 (m, 2H).

Workup

  1. filtrationfilter

Sources & evidence

ORD record
ord-2d62ca9b3ba9405592dbfcfaadfb10ca
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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