Hydrochloric Acid → 2-(3-(4-(1-aminocyclobutyl)phenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-8-yl)-6-fluorobenzoic acid

HRID 1037422Notes

Reaction equation

HRID 1037422 reaction equation
NC1(C2C=CC(C3[C:13](=[O:36])C4C(OC=3C3C=CC=CC=3)=C(C3C(C)=NN(C)C=3C)N=CC=4)=CC=2)CCC1.C([C:39]1[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:40]=1[C:46]1[N:47]=[CH:48][CH:49]=[C:50]2[C:55](=[O:56])[C:54]([C:57]3[CH:62]=[CH:61][C:60]([C:63]4([NH:67]C(=O)OC(C)(C)C)[CH2:66][CH2:65][CH2:64]4)=[CH:59][CH:58]=3)=[C:53]([C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=3)[O:52][C:51]=12)#N.Cl.S(=O)(=O)(O)[OH:83]>O1CCOCC1>[NH2:67][C:63]1([C:60]2[CH:61]=[CH:62][C:57]([C:54]3[C:55](=[O:56])[C:50]4[C:51]([O:52][C:53]=3[C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=3)=[C:46]([C:40]3[CH:41]=[CH:42][CH:43]=[C:44]([F:45])[C:39]=3[C:13]([OH:36])=[O:83])[N:47]=[CH:48][CH:49]=4)=[CH:58][CH:59]=2)[CH2:66][CH2:65][CH2:64]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 670678613-(4-(1-aminocyclobutyl)phenyl)-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-4-oneHCID 86671061tert-butyl (1-(4-(8-(2-cyano-3-fluorophenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 670678982-(3-(4-(1-aminocyclobutyl)phenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-8-yl)-6-fluorobenzoic acid

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-(8-(2-cyano-3-fluorophenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate was reacted with HCl in dioxane and further heated 5 min with concentrated sulphuric acid (0.1 mL) to give the title compound. (5 mg, 20%). 1H NMR (500 MHz, CD3OD): δ 8.65 (d, J=8.2 Hz, 1H), 8.15 (d, J=8.3 Hz, 1H), 7.71-7.65 (m, 1H), 7.58-7.54 (m, 1H), 7.50-7.45 (m, 2H), 7.40-7.25 (m, 6H) 7.20-7.15 (m, 2H), 2.85-2.75 (m, 2H), 2.62-2.55 (m, 2H), 2.28-2.19 (m, 1H), 2.05-1.91 (m, 1H). LCMS (Method I): RT=4.25 min, [M+2]+=508.

Sources & evidence

ORD record
ord-fb2d1976cc14445dbea52ec9df329f1f
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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