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

HRID 2060899ノート

反応式

HRID 2060899 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-130144816ffc4650bbc2d6510b1d6fee
出典データセット
uspto-grants-2012_10
特許番号
US08278442B2

反応ノート

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