Hydrochloric Acid → HCID 86690753, compound

HRID 1471702Notes

Reaction equation

HRID 1471702 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:8]([O:11][CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[N:15][C:14]=2[C:23]2[N:27](COCC[Si](C)(C)C)[N:26]=[CH:25][CH:24]=2)=[CH:9][N:10]=1)[CH:6]=[O:7].Cl>CCO>[NH:27]1[C:23]([C:14]2[N:15]=[CH:16][C:17]3[C:22]([C:13]=2[CH2:12][O:11][C:8]2[C:5]([CH:6]=[O:7])=[CH:4][C:3]([O:2][CH3:1])=[N:10][CH:9]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:24][CH:25]=[N:26]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866907522-methoxy-5-((3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)isonicotinaldehyde

Product 1

HCID 86690753HCID 86690753, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-methoxy-5-((3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)isonicotinaldehyde (10 mg, 0.02 mmol, 1 equiv) suspended in EtOH (1 mL) was added HCl (0.1 mL, 3 N). The solution turned homogeneous and the mixture was stirred at rt overnight. The EtOH was partially removed by blowing in N2 gas and basified to pH 9. The aqueous solution was extracted with EtOAc three times. The organic layer was dried over Na2SO4 and concentrated. The crude was purified on silica gel using MeOH and DCM as eluent to give 5-((3-(1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)-2-methoxyisonicotinaldehyde (6.0 mg, 83%) as a white solid. NMR (400 MHz; CDCl3) δ=10.17 (s, 1H), 9.25 (s, 1H), 8.18 (s, 1H), 8.05 (d, 1H), 7.99 (d, 1H), 7.73 (t, 1H), 7.60-7.68 (m, 2H), 7.03 (s, 1H), 6.70 (d, 1H), 5.85 (s, 2H), 3.85 (s, 3H). LRMS (M+H+) m/z 361.1.

Workup

  1. customThe EtOH was partially removed
  2. extractionThe aqueous solution was extracted with EtOAc three times
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude was purified on silica gel

Sources & evidence

ORD record
ord-c7833c81648443228c192652e56e543d
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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