Hydrochloric Acid → 5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde bis-hydrochloride

HRID 1471712Notes

Reaction equation

HRID 1471712 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[C:14]([CH2:15][O:16][C:17]3[C:22]([CH:23]=[O:24])=[CH:21][C:20]([O:25][CH3:26])=[N:19][CH:18]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[ClH:27]>>[ClH:27].[ClH:27].[CH:1]([N:4]1[C:8]([C:9]2[C:14]([CH2:15][O:16][C:17]3[C:22]([CH:23]=[O:24])=[CH:21][C:20]([O:25][CH3:26])=[N:19][CH:18]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 854729865-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde

Product 1

HCID 866907545-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde bis-hydrochloride

Procedure

5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (980 mg, 2.78 mmol, 1 eq.) in HCl (6 N, 9.2 mL, 20 eq.) solution was freeze at −78° C. The mixture was lyophilized O/N to give 5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde bis-hydrochloride as a yellow solid. 1H NMR (400 MHz, D2O) δ 8.85 (dd, J=5.7, 1.3 Hz, 1H), 8.78 (d, J=8.2 Hz, 1H), 8.12 (dd, J=8.1, 5.7 Hz, 1H), 7.76 (s, 1H), 7.72 (d, J=2.0 Hz, 1H), 7.46 (s, 1H), 6.65 (d, J=2.1 Hz, 1H), 6.09 (s, 1H), 5.09 (s, 2H), 4.24 (sep, J=6.6 Hz, 1H), 4.04 (s, 3H), 1.26 (d, J=6.6 Hz, 7H). LRMS (M+H+) m/z 353.1.

Workup

  1. customat −78° C

Sources & evidence

ORD record
ord-b68c84cdaf0643e5bcc1cb39680aec7a
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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