tert-Butyl 1-(4-(8-(2-hydroxyethoxy)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate → 3-(4-(1-aminocyclobutyl)phenyl)-8-(2-hydroxyethoxy)-2-phenyl-4H-pyrano[2,3-c]pyridin-4-one

HRID 1037428Notes

Reaction equation

HRID 1037428 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.[OH:37][CH2:38][CH2:39][O:40][C:41]1[N:42]=[CH:43][CH:44]=[C:45]2[C:50](=[O:51])[C:49]([C:52]3[CH:57]=[CH:56][C:55]([C:58]4([NH:62]C(=O)OC(C)(C)C)[CH2:61][CH2:60][CH2:59]4)=[CH:54][CH:53]=3)=[C:48]([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[O:47][C:46]=12>>[NH2:62][C:58]1([C:55]2[CH:54]=[CH:53][C:52]([C:49]3[C:50](=[O:51])[C:45]4[C:46]([O:47][C:48]=3[C:70]3[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=3)=[C:41]([O:40][CH2:39][CH2:38][OH:37])[N:42]=[CH:43][CH:44]=4)=[CH:57][CH:56]=2)[CH2:59][CH2:60][CH2:61]1

Participants

3

Reactant 2

HCID 67067725tert-Butyl 1-(4-(8-(2-hydroxyethoxy)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamateHCID 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 670679473-(4-(1-aminocyclobutyl)phenyl)-8-(2-hydroxyethoxy)-2-phenyl-4H-pyrano[2,3-c]pyridin-4-one

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-hydroxyethoxy)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate was reacted to give the title compound. (10 mg, 62%). 1H NMR (400 MHz, CD3OD): δ 8.15 (d, 1H), 7.55 (d, 1H), 7.49-7.31 (m, 9H), 4.68-4.65 (m, 2H), 3.95-4.01 (m, 2H), 2.82-2.75 (m, 2H), 2.63-2.52 (m, 2H), 2.30-2.19 (m, 1H), 2.03-1.92 (m, 1H). LCMS (Method I): RT=3.83 min, [M+2]+=430.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-6901a82a41884d6a98197e4db02c8e2c
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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