Hydrochloric Acid → HCID 68227208, compound

HRID 1037431Notes

Reaction equation

HRID 1037431 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:13](=[O:31])[C:14]4[C:15]([O:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:16]([CH2:20][CH2:21]Cl)[N:17]=[CH:18][CH:19]=4)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.C(C1N=CC=C2C(=O)C(C3C=CC(C4(NC(=O)OC(C)(C)C)CCC4)=CC=3)=C(C3C=CC=CC=3)OC=12)C.Cl>O1CCOCC1>[NH2:1][C:2]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[C:13](=[O:31])[C:14]4[C:15]([O:23][C:24]=3[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:16]([CH2:20][CH3:21])[N:17]=[CH:18][CH:19]=4)=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67068011HCID 67068011, compoundHCID 68227335HCID 68227335, compound

Product 1

HCID 68227208HCID 68227208, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following same procedure used to prepare 3-(4-(1-aminocyclobutyl)phenyl)-8-(2-chloroethyl)-2-phenyl-4H-pyrano[2,3-c]pyridin-4-one, tert-butyl 1-(4-(8-ethyl-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate was reacted with 4 M HCl in 1,4-dioxane to give the title compound (5 mg, 62%). 1H NMR (500 MHz, CD3OD): δ 8.61 (d, 1H), 7.95 (d, 1H), 7.51-7.30 (m, 9H), 3.42-3.35 (m, 2H), 2.75-2.67 (m, 2H), 2.55-2.42 (m, 2H), 2.28-2.12 (m, 1H), 1.98-1.88 (m, 1H). 1.5 (t, 3H). LCMS (Method I): RT=4.31 min, [M+2]+=398.

Sources & evidence

ORD record
ord-e7e7a114d8b34237be7daa3ba79c32ba
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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