Acetic Acid → HCID 178448124、化合物

HRID 2060900ノート

反応式

HRID 2060900 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.Cl.[CH:24]([C@H:27]1[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29][CH2:28]1)([CH3:26])[CH3:25].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH:24]([C@H:27]1[CH2:32][CH2:31][C@H:30]([NH:33][CH2:1][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]([O:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=3)=[CH:5][N:4]=2)[CH2:29][CH2:28]1)([CH3:26])[CH3:25]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 594013146-(1-Formylisoquinolin-4-yloxy)nicotinamideHCID 178448120HCID 178448120、化合物

生成物 1

HCID 178448124HCID 178448124、化合物

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a suspension of 6-(1-formylisoquinolin-4-yloxy)nicotinamide (Preparation 20) (150 mg, 0.51 mmol) and trans-4-isopropylcyclohexylamine hydrochloride (Preparation 9) (273 mg, 1.53 mmol) in 1,2-dichloroethane (10 mL) under argon was added acetic acid (30 μL, 0.51 mmol) followed by NaBH(OAc)3 (325 mg, 1.53 mmol). The mixture was stirred at rt for 16 h then the reaction solvent was removed in vacuo. The residue was partitioned between EtOAc (50 mL) and NaHCO3 (30 mL), and the organic phase washed with NaHCO3 (30 mL), brine (30 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (SiO2, NH4OH:MeOH:DCM 0.5:5:95) to give the title compound: RT=2.85 min; m/z (ES+)=419.3 [M+H]+.

後処理

  1. customthe reaction solvent was removed in vacuo
  2. customThe residue was partitioned between EtOAc (50 mL) and NaHCO3 (30 mL)
  3. washthe organic phase washed with NaHCO3 (30 mL), brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo
  6. customthe residue purified by column chromatography (SiO2, NH4OH:MeOH:DCM 0.5:5:95)

出典と根拠

ORDレコード
ord-2e84c190d8e44f55b91efa0dba6b82e9
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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