3-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-one → 7-[4-(1-Amino-cyclobutyl)-phenyl]-1,2-dimethyl-8-phenyl-1H-chromeno[7,8-d]imidazol-6-one

HRID 1037369Notes

Reaction equation

HRID 1037369 reaction equation
NC1(C2C=CC(C3C(=O)C4C(OC=3C3C=CC=CC=3)=C3C(=CC=4)NN=C3)=CC=2)CCC1.C(OC(=O)[NH:38][C:39]1([C:43]2[CH:48]=[CH:47][C:46]([C:49]3[C:54](=[O:55])[C:53]4[CH:56]=[CH:57][C:58]5[N:59]=[C:60]([CH3:64])[N:61]([CH3:63])[C:62]=5[C:52]=4[O:51][C:50]=3[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:45][CH:44]=2)[CH2:42][CH2:41][CH2:40]1)(C)(C)C>>[NH2:38][C:39]1([C:43]2[CH:44]=[CH:45][C:46]([C:49]3[C:54](=[O:55])[C:53]4[CH:56]=[CH:57][C:58]5[N:59]=[C:60]([CH3:64])[N:61]([CH3:63])[C:62]=5[C:52]=4[O:51][C:50]=3[C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)=[CH:47][CH:48]=2)[CH2:40][CH2:41][CH2:42]1

Participants

3

Reactant 2

HCID 510295913-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-oneHCID 67067933{1-[4-(1,2-Dimethyl-6-oxo-8-phenyl-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510304207-[4-(1-Amino-cyclobutyl)-phenyl]-1,2-dimethyl-8-phenyl-1H-chromeno[7,8-d]imidazol-6-oneYield 80%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-one, {1-[4-(1,2-dimethyl-6-oxo-8-phenyl-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a white solid (26 mg, 80%). 1H NMR (400 MHz, DMSO-d6): δ 7.84 (d, J=8.4 Hz, 1H), 7.61 (d, J=8.4 Hz, 1H), 7.52-7.49 (m, 2H), 7.44-7.34 (m, 5H), 7.16-7.13 (m, 2H), 4.09 (s, 3H), 2.61 (s, 3H), 2.41-2.33 (m, 2H), 2.12-2.03 (m, 2H), 2.03-1.93 (m, 1H), 1.70-1.61 (m, 1H). LCMS (Method E): RT=2.71 min, [M+H]+=436.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-897ffe5addc0476eb81466cbbf4748a5
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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