Methanol → HCID 68154076, compound

HRID 341077Notes

Reaction equation

HRID 341077 reaction equation
[O:1]=[C:2]1[C:6]2=[CH:7][N:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4][N:3]1[C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([OH:31])=[O:30].CO.[CH3:38][Si](C=[N+]=[N-])(C)C>O1CCCC1>[O:1]=[C:2]1[C:6]2=[CH:7][N:8]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:20][CH:21]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4][N:3]1[C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([O:31][CH3:38])=[O:30]

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 52913020HCID 52913020, compound

Product 1

HCID 68154076HCID 68154076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzoic acid (Example 611, 30 mg, 0.065 mmol) was dissolved in tetrahydrofuran (1 mL) and methanol (1 mL) and treated with (trimethylsilyl)diazomethane (0.065 mL, 2 M diethyl ether solution, 0.13 mmol, 2 equiv). After stirring for 30 minutes, the mixture was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (80:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.15 (1H s), 8.46 (1H, d, J=2.5 Hz), 8.21 (1H, dd, J=7.8, 1.4 Hz), 7.83 (2H, d, J=8.8 Hz), 7.79 (1H, m), 7.77 (1H, d, J=2.3 Hz), 7.73-7.61 (3H, m), 7.56 (1H, t, J=7.7 Hz), 7.46 (2H, d, 8.7 Hz), 7.41 (1H, td, J=7.7, 1.1 Hz), 6.53 (1H, dd, J=2.4, 1.8 Hz), 5.77 (2H, s), 3.67 (3H, s) ppm; low resolution mass spectrometry (ES+) m/z 476.0 [(M+H)+; calculated for C28H22N5O3: 476.2].

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was purified by preparative reverse phase HPLC (80:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-0aecb5ebe2f2459aa02e2eb1aff617b0
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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