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

HRID 1037386Notes

Reaction equation

HRID 1037386 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]=[CH:60][N:61]([CH3:63])[C:62]=5[C:52]=4[O:51][C:50]=3[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=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]=[CH:60][N:61]([CH3:63])[C:62]=5[C:52]=4[O:51][C:50]=3[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=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 68227562{1-[4-(1-Methyl-6-oxo-8-phenyl-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510305177-[4-(1-Amino-cyclobutyl)-phenyl]-1-methyl-8-phenyl-1H-chromeno[7,8-d]imidazol-6-oneYield 85%

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-methyl-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 (43 mg, 85%). 1H NMR (400 MHz, DMSO-d6): δ 8.44 (s, 1H), 7.88 (d, J=9.2 Hz, 1H), 7.73 (d, J=9.2 Hz, 1H), 7.54-7.50 (m, 2H), 7.44-7.34 (m, 5H), 7.18-7.13 (m, 2H), 4.21 (s, 3H), 2.42-2.34 (m, 2H), 2.12-2.04 (m, 2H), 2.04-1.94 (m, 1H), 1.70-1.59 (m, 1H). LCMS (Method E): RT=2.86 min, [M+H]+=422.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-dca4b0d09c9344ee84c4017c9a127900
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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