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

HRID 1037362Notes

Reaction equation

HRID 1037362 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[NH:59][C:60](=[O:63])[NH:61][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[NH:59][C:60](=[O:63])[NH:61][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)[CH2:42][CH2:41][CH2:40]1

Participants

3

Reactant 2

HCID 510295913-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-oneHCID 67067863{1-[4-(2,6-Dioxo-8-phenyl-1,2,3,6-tetrahydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510304177-[4-(1-Amino-cyclobutyl)-phenyl]-8-phenyl-1,3-dihydro-chromeno[7,8-d]imidazole-2,6-dioneYield 75%

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-(2,6-dioxo-8-phenyl-1,2,3,6-tetrahydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a yellow solid (41 mg, 75%). 1H NMR (400 MHz, DMSO-d6): δ 7.71 (d, J=8.3 Hz, 1H), 7.63 (s, 1H), 7.53-7.49 (m, 2H), 7.44-7.38 (m, 3H), 7.35-7.30 (m, 2H), 7.22-7.19 (m, 2H), 7.14 (d, J=8.3 Hz, 1H), 7.01 (s, 1H), 2.50-2.43 (m, 2H), 2.32-2.22 (m, 2H), 2.12-2.01, (m, 1H), 1.78-1.68 (m, 1H). LCMS (Method E): RT=2.63 min, [M+H]+=424.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-5c7ccb36f38b43efb65ae30006d6a947
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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