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

HRID 269997
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HRID 269997 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-37e1a8ecdc354f32b9f787524ef144c3
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07449477B2

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