Triethylamine → HCID 60029934, compound

HRID 496432Notes

Reaction equation

HRID 496432 reaction equation
[NH2:1][C:2]1[C:11]([O:12][C@H:13]([CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:23].[C:24]1([C:34](O)=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][N:25]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:18]1([CH2:17][C@@H:13]([O:12][C:11]2[CH:10]=[CH:9][C:8]3[C:7](=[O:23])[CH2:6][CH2:5][CH2:4][C:3]=3[C:2]=2[NH:1][C:34]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][N:25]=2)=[O:35])[CH:14]([CH3:16])[CH3:15])[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 68092Isoquinoline-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 60029917HCID 60029917, compound

Product 1

HCID 60029934HCID 60029934, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-amino-6-((S)-1-imidazol-1-ylmethyl-2-methyl-propoxy)-3,4-dihydro-2H-naphthalen-1-one (105 mg, 0.335 mmol) and 1-isoquinoline carboxylic acid (70 mg, 0.402 mmol) in DMF (3 mL) was added Et3N (56 μL, 0.402 mmol) followed by HATU (153 mg, 0.402 mmol). The reaction was stirred at RT overnight. The DMF was removed under reduced pressure. The residue was diluted with EtOAc and washed with H2O, saturated aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated. Purification by chromatography (5% MeOH/EtOAc with 1% NH4OH) afforded the title compound as a foam (66 mg, 0.141 mmol, 42%). The structure was confirmed by NMR and mass spectrometry. MS m/z 469 (M++H).

Workup

  1. customThe DMF was removed under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washwashed with H2O, saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by chromatography (5% MeOH/EtOAc with 1% NH4OH)

Sources & evidence

ORD record
ord-46f5eb4aa1494e44ad42982e961eb1af
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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