Acetic Acid → 6-{1-[(3-Methylbutylamino)methyl]isoquinolin-4-yloxy}nicotinamide

HRID 2060899노트

반응식

HRID 2060899 반응식
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=2)=[CH:5][N:4]=1)=O.[CH3:23][CH:24]([CH3:28])[CH2:25][CH2:26][NH2:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH3:23][CH:24]([CH3:28])[CH2:25][CH2:26][NH:27][CH2:1][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=2)=[CH:5][N:4]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 7894IsoamylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 594013146-(1-Formylisoquinolin-4-yloxy)nicotinamide

생성물 1

HCID 251214806-{1-[(3-Methylbutylamino)methyl]isoquinolin-4-yloxy}nicotinamide

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To 6-(1-formylisoquinolin-4-yloxy)nicotinamide (Preparation 20) (130 mg, 0.44 mmol) in dichloroethane (8 mL) was added 3-methylbutylamine (154 μL, 1.33 mmol), NaBH(OAc)3 (282 mg, 1.33 mmol) and acetic acid (76 μL, 1.33 mmol). The mixture was stirred for 16 h. NaHCO3 (50 mL) was added and the mixture extracted with EtOAc (3×40 mL). The organic phase was washed with water (30 mL), brine (30 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (0.5 NH3: 5 MeOH: 95 DCM) to give the title compound: RT=2.48 min; m/z (ES+)=365.2 [M+H]+.

후처리

  1. extractionthe mixture extracted with EtOAc (3×40 mL)
  2. washThe organic phase was washed with water (30 mL), brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customSolvent was removed in vacuo
  5. customthe residue purified by column chromatography (0.5 NH3: 5 MeOH: 95 DCM)

출처 및 근거

ORD 기록
ord-130144816ffc4650bbc2d6510b1d6fee
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278442B2

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