4'-Methoxy-(1,1'-biphenyl)-4-carboxaldehyde → N1-(isothiazolo[5,4-b]pyrazin-3-yl)-N3-((4'-methoxybiphenyl-4-yl)methyl)propane-1,3-diamine

HRID 502573노트

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HRID 502573 반응식
[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][N:9]=[C:4]2[C:3]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])=[N:2]1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][N:9]=[C:4]2[C:3]([NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:29][C:26]2[CH:25]=[CH:24][C:23]([C:20]3[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=3)=[CH:28][CH:27]=2)=[N:2]1

참가 물질

6

반응물 3

HCID 13944874'-Methoxy-(1,1'-biphenyl)-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58726848N1-(isothiazolo[5,4-b]pyrazin-3-yl)propane-1,3-diamine

생성물 1

HCID 58726860N1-(isothiazolo[5,4-b]pyrazin-3-yl)-N3-((4'-methoxybiphenyl-4-yl)methyl)propane-1,3-diamine수율 12.6%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

N1-(Isothiazolo[5,4-b]pyrazin-3-yl)propane-1,3-diamine (410 mg, 1.96 mmol) and 4′-methoxybiphenyl-4-carbaldehyde (410 mg, 1.96 mmol) were combined in 1,2-dichloroethane (8 mL) and treated with sodium triacetoxyborohydride (506 mg, 2.35 mmol). The mixture was shaken at room temperature for 3 h. The reaction was diluted with methylene chloride, quenched with water and the layers were separated. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography, on silica gel, eluting with methylene chloride:methanol to yield N1-(isothiazolo[5,4-b]pyrazin-3-yl)-N3-((4′-methoxybiphenyl-4-yl)methyl)propane-1,3-diamine (100 mg) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): 8.79 (d, 1H), 8.72 (d, 1H), 7.90 (t, 1H), 7.54 (m, 4H), 7.40 (d, 2H), 6.98 (d, 2H), 3.82 (s, 2H), 3.80 (s, 3H), 3.48 (t, 2H), 2.70 (m, 3H), 1.85 ppm (m, 2H). MW=405 confirmed by LC-MS, tr=9.59 min (Method Y) MH+=404-406.

후처리

  1. customquenched with water
  2. customthe layers were separated
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by flash column chromatography, on silica gel
  7. washeluting with methylene chloride

출처 및 근거

ORD 기록
ord-f4ed6acbf6114aef962dc4611c38e12a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776847B2

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