1,2-Dichloroethane → 7-Phenyl-isoquinoline-5-sulfonic acid [2-(3-naphthalen-1-yl-propylamino)-ethyl]-amide dihydrochloride

HRID 269997Notes

Reaction equation

HRID 269997 reaction equation
[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]=[CH:20][CH:19]=2)[CH:17]=1)(=[O:7])=[O:6].[C:24]1([CH2:34][CH2:35][CH:36]=O)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:52]CCCl>CO>[ClH:52].[ClH:52].[C:24]1([CH2:34][CH2:35][CH2:36][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]=[CH:20][CH:19]=3)[CH:17]=2)(=[O:7])=[O:6])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 110414091-NaphthalenepropanalHCID 112903567-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide

Product 1

HCID 1317271767-Phenyl-isoquinoline-5-sulfonic acid [2-(3-naphthalen-1-yl-propylamino)-ethyl]-amide dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir a mixture of 7-phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide (0.25 mmol, 1.0 eq) and 3-naphthalen-1-yl-propionaldehyde (0.25 mmol, 1.0 eq) in 1,2-dichloroethane (DCE) (2.0 mL) at room temperature for six (6) hours, and then add sodium triacetoxyborohydride (0.6 mmol, 2.4 eq). Stir overnight, then dilute the mixture with CH3OH, and apply to a cation exchange column (10 g), wash with a mixture of, CH3OH and CH2Cl2 (1:1), then NH3 (2.0 M in CH3OH). Purify the residue on silica gel (gradient 10% CH3OH in CH2Cl2) to give 100 mg the free amine product as oil. Dissolve the free amine in CH3OH (15 mL) and treat dropwise with 37% HCl aqueous solution (1.0 mL) with stirring. Concentrate the resultant solution and dried under vacuum at 37° C. to give the title compound as a white powder. 1H NMR (DMSO-d6, 400 MHz): 9.65 (1H, s), 8.85 (2H, br), 8.75 (1H, s), 8.69 (1H, d, J=6.0 Hz), 8.64 (1H,s), 8.53 (1H, t, J=6.0 Hz), 8.07 (1H, d, J=8.0 Hz), 7.91 (2H, d, J=7.6 Hz), 7.78 (1H, d, J=8.0 Hz), 7.49-7.61(4H, s), 7.46 (1H, d, J=7.6 Hz), 7.35 (1H, d, J=7.2 Hz), 3.12-3.15 (2H, m), 3.07 (2H, t, J=7.6 Hz), 2.95-3.02 (4H, m), 1.93-1.99 (2H, m). IS-MS, m/e 582.58 (m+1)

Workup

  1. stirringStir overnight
  2. washapply to a cation exchange column (10 g), wash with a mixture of, CH3OH and CH2Cl2 (1:1)
  3. customPurify the residue on silica gel (gradient 10% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-37e1a8ecdc354f32b9f787524ef144c3
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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