HCID 13007823, compound → HCID 136341444, compound

HRID 1745795Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([NH2:15])[CH:9]=2)=[CH:4][CH:3]=1.O[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:20][C:19](=[O:27])[CH:18]=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C.CCCCCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]3[N:14]=[C:17]([C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[OH:20])[CH2:18][C:19](=[O:27])[NH:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1.[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]3[NH:14][C:19](=[O:27])[CH2:18][C:17]([C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[OH:20])=[N:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4′-fluoro-biphenyl-3,4-diamine (prepared from (3-amino-4′-fluoro-biphenyl-4-yl)-carbamic acid tert.-butyl ester (Example G39) by treatment with TFA) (121 mg, 0.6 mmol) and 4-hydroxycoumarin (97 mmol, 0.6 mmol) in xylene (8 mL) was heated to 130° C. for 6 h. A yellow precipitate started to form after ca. 1 h. The mixture was cooled to 23° C., diluted with ethyl acetate (8 mL) and hexane (8 mL) and stirring was continued for 15 min. The precipitate was collected by filtration and triturated with ethyl acetate/hexane (1:1) to give the title compound as a mixture with the isomeric 7-(4-fluoro-phenyl)-4-(2-hydroxy-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one as yellow solid (117 mg).

Workup

customto form after ca. 1 h
temperatureThe mixture was cooled to 23° C.
filtrationThe precipitate was collected by filtration
customtriturated with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record: ord-97fb4f77f65b48e086f054efdb979b7f
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07018998B2

Reaction notes

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