Water → HCID 11624421, compound

HRID 506991Notes

Reaction equation

HRID 506991 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=O)[C:9]2=[O:12])=[CH:4][CH:3]=1.CN(C(ON1N=[N:38][C:33]2[CH:34]=[CH:35][CH:36]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CCC1.O>CN(C=O)C>[CH:33]1([NH:38][C:16](=[O:18])[C:15]2[CH:19]=[CH:20][C:21]([CH3:22])=[C:13]([N:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=4)[C:9]3=[O:12])[CH:14]=2)[CH2:34][CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 962WaterHCID 75645CyclobutylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 670185873-(7-hydroxy-1-oxo-1H-isoquinolin-2-yl)-4-methylbenzoic acid

Product 1

HCID 11624421HCID 11624421, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(7-Hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (295 mg), HATU (406 mg) and cyclobutylamine (0.43 ml) were dissolved in DMF (25 ml) and stirred at room temperature for 18 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (magnesium sulfate) and concentrated. The residue was purified by column chromatography with ethyl acetate to give N-cyclobutyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as a white solid (150 mg); NMR Spectrum: (DMSOd6) 1.35 (m, 2H), 2.03 (m, 2H), 2.10 (s, 3H), 2.20 (m, 2H), 4.40 (m, 1H), 6.65 (d, 1H), 7.12 (d, 1H), 7.22 (m, 1H), 7.46 (d, 1H), 7.60 (m, 2H), 7.76 (s, 1H), 7.85 (d, 1H) 8.60 (d, 1H), 10.00 (s, 1H); Mass Spectrum: M+H+ 349.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-d2a9190bf61e47229e00cf6c36eea066
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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