Hydrochloric Acid → HCID 86690737, compound

HRID 1471686Notes

Reaction equation

HRID 1471686 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:8]([O:11][CH2:12][C:13]2[C:14]([C:19]3[N:23](COCC[Si](C)(C)C)[N:22]=[CH:21][CH:20]=3)=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:9][N:10]=1)[CH:6]=[O:7].[ClH:32]>CCO>[ClH:32].[ClH:32].[NH:23]1[C:19]([C:14]2[C:13]([CH2:12][O:11][C:8]3[C:5]([CH:6]=[O:7])=[CH:4][C:3]([O:2][CH3:1])=[N:10][CH:9]=3)=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:20][CH:21]=[N:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86690738HCID 86690738, compound

Product 1

HCID 86690737HCID 86690737, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-methoxy-5-((2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde (120 mg, 0.27 mmol, 1 equiv) suspended in EtOH (1 mL) was added HCl (1.0 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 the precipitate was collected. The solid was washed with acetonitrile and EtOAc and dried under high vacuo to give 5-((2-(1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde dihydrochloride (100 mg, 96%) as a white solid. 1H NMR (400 MHz; DMSO, 80° C.) δ=10.27 (s, 1H), 8.68 (br, 1H), 8.32 (br, 1H), 8.22 (s, 1H), 7.82 (br, 1H), 7.57 (br, 1H), 7.00 (br, 2H), 5.75 (s, 2H), 3.89 (s, 3H). LRMS (M+H+) m/z 311.1.

Workup

  1. customThe EtOH was partially removed
  2. customthe precipitate was collected
  3. washThe solid was washed with acetonitrile and EtOAc
  4. customdried under high vacuo

Sources & evidence

ORD record
ord-51a3402dbd2e47c38a19a9513e399b94
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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