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

HRID 1037423Notes

Reaction equation

HRID 1037423 reaction equation
NC1(C2C=CC(C3C(=O)C4C(OC=3C3C=CC=CC=3)=C(C3C(C)=NN(C)C=3C)N=CC=4)=CC=2)CCC1.[N+:37]([C:39]1[CH:40]=[C:41]([C:45]2[N:46]=[CH:47][CH:48]=[C:49]3[C:54](=[O:55])[C:53]([C:56]4[CH:61]=[CH:60][C:59]([C:62]5([NH:66]C(=O)OC(C)(C)C)[CH2:65][CH2:64][CH2:63]5)=[CH:58][CH:57]=4)=[C:52]([C:74]4[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=4)[O:51][C:50]=23)[CH:42]=[CH:43][CH:44]=1)#[C-:38].Cl>O1CCOCC1>[NH2:66][C:62]1([C:59]2[CH:58]=[CH:57][C:56]([C:53]3[C:54](=[O:55])[C:49]4[C:50]([O:51][C:52]=3[C:74]3[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=3)=[C:45]([C:41]3[CH:42]=[CH:43][CH:44]=[C:39]([N+:37]#[C-:38])[CH:40]=3)[N:46]=[CH:47][CH:48]=4)=[CH:61][CH:60]=2)[CH2:63][CH2:64][CH2:65]1

Participants

5

Reactant 3

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-oneHCID 86671063tert-butyl (1-(4-(8-(3-isocyanophenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 866710623-(4-(1-aminocyclobutyl)phenyl)-8-(3-isocyanophenyl)-2-phenyl-4H-pyrano[2,3-c]pyridin-4-oneYield 15%

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-(3-isocyanophenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate was reacted with HCl in dioxane. The product was purified by preparative HPLC to give the title compound (5 mg, 15%). 1H NMR (500 MHz, CD3OD): δ 8.69 (d, J=8.2 Hz, 1H), 8.41 (s, 1H), 8.32-8.29 (m, 1H), 8.05 (d, J=8.3 Hz, 1H), 7.79-7.75 (m, 1H), 7.65-7.61 (m, 1H), 7.40-7.19 (m, 9H), 2.75-2.65 (m, 2H), 2.45-2.40 (m, 2H), 2.18-2.12 (m, 1H), 1.91-1.82 (m, 1H). LC-MS (Method I): RT=4.68 min, [M+2]+=471.

Workup

  1. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-e76b77aec7164ea899c6a7a63cf0fe13
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…