Dichloromethane → 7-(3-Difluoromethylphenyl)-isoquinoline-5-sulfonic acid {2-[3-(4-nitro-phenyl)-propylamino]-ethyl}-amide, dihydrochloride salt

HRID 270001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270001
[NH2:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][C:14]=2[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([F:26])[F:25])[CH:19]=2)[CH:17]=1)(=[O:7])=[O:6].[N+:27]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH:38]=O)=[CH:32][CH:31]=1)([O-:29])=[O:28].[BH4-].[Na+].[Cl:42]CCl>CO>[ClH:42].[ClH:42].[N+:27]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38][NH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]2[C:9]3[CH:10]=[CH:11][N:12]=[CH:13][C:14]=3[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([F:26])[F:25])[CH:19]=3)[CH:17]=2)(=[O:7])=[O:6])=[CH:32][CH:31]=1)([O-:29])=[O:28]

Komponenten

6

Edukt 4

HCID 6344Dichloromethane2×HCID 4311764Sodium borohydrideHCID 112803467-(3-Difluoromethylphenyl)-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amideHCID 112982903-(4-Nitrophenyl)propanal

Produkt 1

HCID 1317271787-(3-Difluoromethylphenyl)-isoquinoline-5-sulfonic acid {2-[3-(4-nitro-phenyl)-propylamino]-ethyl}-amide, dihydrochloride saltAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Dissolve 7-(3-Difluoromethylphenyl)-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide (0.060 g, 0.16 mmol) in a mixture of dichloromethane and methanol (5:1, 15 mL). To the solution add 3-(4-nitrophenyl)-propionaldehyde (0.043 g, 0.24 mmol) as a solution in dichloromethane and stir overnight. Add sodium borohydride (0.025 g, 0.67 mmol). Evaporate the solvent and purify the residue by silica gel chromatography to give the free base of the desired compound (0.042 g, 48% yield): 1H NMR (CDCl3/CD3OD): δ9.40 (s, 1H), 8.70 (m, 2H), 8.40 (m, 2H), 8.10 (m, 2H), 7.85 (m, 2H), 7.62 (m, 2H), 7.26 (m, 2H), 6.73 (t, J=52.1 Hz, 1H), 3.00 (m, 2H), 2.64 (m, 4H), 2.42 (t, J=7.0 Hz, 2H), 1.67 (m, 2H). ESIMS: m/z 541 (M+H)+. Form the dihydrochloride salt by suspending the free base in ethyl acetate, cooling to 0° C., and adding 4M HCl in 1,4-dioxane dropwise. Filter the precipitate and wash with dichloromethane then dry in vacuum to give the desired compound.

Aufarbeitung

  1. customEvaporate the solvent
  2. custompurify the residue by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-260ca7e9980743b48bff75d31e580646
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449477B2

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