Acetic Acid → HCID 178448124, compound

HRID 2060900Notes

Reaction equation

HRID 2060900 reaction equation
[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]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 594013146-(1-Formylisoquinolin-4-yloxy)nicotinamideHCID 178448120HCID 178448120, compound

Product 1

HCID 178448124HCID 178448124, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-2e84c190d8e44f55b91efa0dba6b82e9
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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