Hydrochloric Acid → 3-(4-(1-aminocyclobutyl)phenyl)-2-phenyl-8-(pyridin-3-yl)-4H-pyrano[2,3-c]pyridin-4-one hydrochloride

HRID 1037425Notes

Reaction equation

HRID 1037425 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:13](=[O:36])[C:14]4[C:15]([O:28][C:29]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:16]([C:20]3[C:21]([CH3:27])=N[N:23]([CH3:26])[C:24]=3C)[N:17]=[CH:18][CH:19]=4)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.[ClH:37]>O1CCOCC1>[ClH:37].[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:13](=[O:36])[C:14]4[C:15]([O:28][C:29]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:16]([C:20]3[CH:24]=[N:23][CH:26]=[CH:27][CH:21]=3)[N:17]=[CH:18][CH:19]=4)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670678613-(4-(1-aminocyclobutyl)phenyl)-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-4-one

Product 1

HCID 670680453-(4-(1-aminocyclobutyl)phenyl)-2-phenyl-8-(pyridin-3-yl)-4H-pyrano[2,3-c]pyridin-4-one hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following the procedure used to prepare 3-(4-(1-aminocyclobutyl)phenyl)-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-4-one, tert-butyl 1-(4-(4-oxo-2-phenyl-8-(pyridin-3-yl)-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl carbamate was reacted with HCl in dioxane to give the title compound as the HCl salt (12 mg, 70%). 1H NMR (500 MHz, CD3OD): δ 9.49 (bs, 1H), 9.25-9.20 (m, 1H), 8.90-8.85 (m, 1H), 8.78 (m, 1H), 8.25-8.20 (m, 2H), 8.15 (m, 1H), 7.91-7.80 (m, 2H), 7.41-7.20 (m, 6H), 2.71-2.62 (m, 2H), 2.55-2.45 (m, 2H), 2.20-2.14 (m, 1H), 1.88-1.82 (m, 1H). LCMS (Method I): RT=4.06 min, [M+2]+=447.

Sources & evidence

ORD record
ord-fdf01319e64e4a169a68c0e6d0dd7d28
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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