3-(4-(1-aminocyclobutyl)phenyl)-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-4-one → 3-(4-(1-aminocyclobutyl)phenyl)-2,8-diphenyl-4H-pyrano[2,3-c]pyridin-4-one

HRID 1037426Notes

Reaction equation

HRID 1037426 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.[O:37]=[C:38]1[C:47]2[C:42](=[C:43]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:44]=[CH:45][CH:46]=2)[O:41][C:40]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[C:39]1[C:60]1[CH:65]=[CH:64][C:63]([C:66]2([NH:70]C(=O)OC(C)(C)C)[CH2:69][CH2:68][CH2:67]2)=[CH:62][CH:61]=1>>[NH2:70][C:66]1([C:63]2[CH:62]=[CH:61][C:60]([C:39]3[C:38](=[O:37])[C:47]4[C:42]([O:41][C:40]=3[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[C:43]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:44]=[CH:45][CH:46]=4)=[CH:65][CH:64]=2)[CH2:69][CH2:68][CH2:67]1

Participants

3

Reactant 2

HCID 670678613-(4-(1-aminocyclobutyl)phenyl)-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-4-oneHCID 86671064tert-Butyl (1-(4-(4-oxo-2,8-diphenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 680548093-(4-(1-aminocyclobutyl)phenyl)-2,8-diphenyl-4H-pyrano[2,3-c]pyridin-4-oneYield 15%

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-2,8-diphenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate was reacted give the title compound (5 mg, 15%). 1H NMR (500 MHz, CD3OD): δ 8.65 (d, J=5.1 Hz, 1H), 7.96 (d, J=5.1 Hz, 1H), 7.89-7.85 (m, 2H), 7.46-7.15 (m, 12H), 2.69-2.63 (m, 2H), 2.49-2.52 (m, 2H), 2.20-2.11 (m, 1H), 1.92-1.78 (m, 1H). LCMS (Method I): RT=4.67 min, [M+2]+=446.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-ba301185422b4d01b2e8a9ac7d8a750a
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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