Hydrochloric Acid → 4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzaldehyde

HRID 1920033

Reaction equation

[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[C:28]3[CH:29]=[N:30][NH:31][CH:32]=3)[N:13]=2)=[CH:8][CH:7]=1.Cl>CN1C(=O)CCC1>[C:22]1([C:21]2[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][CH:10]=3)=[N:13][C:14]3[C:19]([CH:20]=2)=[C:18]([C:28]2[CH:29]=[N:30][NH:31][CH:32]=2)[N:17]=[CH:16][CH:15]=3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridine (1-2) (1.0 g, 2.4 mmol) in NMP (25 mL) was added 6N HCl (10 mL). The reaction was heated at 80° C. for 1 hour. The reaction mixture was cooled to room temperature, slowly quenched into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum to give 4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzaldehyde (1-3) as a white solid. MS (M+H)+: calculated 377.42; found 377.51

Workup

temperatureThe reaction mixture was cooled to room temperature
customslowly quenched into saturated sodium bicarbonate
extractionextracted with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-286fe8e00f3b4f1482a70e9aeca62605
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168652B2

Linked notes

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