7-Amino-3-bromo-2-phenyl-1-benzopyran-4-one → {1-[4-(7-Amino-4-oxo-2-phenyl-4H-1-benzopyran-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037270

Reaction equation

HRID 1037270 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23](=[O:24])[C:22]4[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=4[O:20][C:19]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH2:36]C1C=CC2C(=O)C(Br)=C(C3C=CC=CC=3)OC=2C=1>>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23](=[O:24])[C:22]4[CH:25]=[CH:26][C:27]([NH2:36])=[CH:28][C:21]=4[O:20][C:19]=3[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 670676767-Amino-3-bromo-2-phenyl-1-benzopyran-4-oneHCID 67067804{1-[4-(4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 67067858{1-[4-(7-Amino-4-oxo-2-phenyl-4H-1-benzopyran-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 19%

Procedure

Following the procedure used for {1-[4-(4-oxo-2-phenyl-4H-1-benzopyran-3-yl)phenyl]-cyclobutyl}-carbamic acid tert-butyl ester, 7-amino-3-bromo-2-phenyl-1-benzopyran-4-one (28.4 mg, 0.09 mmol) was reacted to give the title compound as a yellow solid (6.3 mg, 19%). 1H-NMR (400 MHz, CDCl3) δ 8.05 (d, 1H), 7.64 (d, 2H), 7.50 (d, 2H), 7.45 (d, 2H), 7.35 (dd, 1H), 7.31 (dd, 2H), 6.82 (d, 1H), 6.74 (s, 1H), 5.28 (bs, 1H), 4.11 (bs, 2H), 2.62-2.65 (m, 4H), 2.15-2.19 (m, 1H), 1.90-1.97 (m, 1H) 1.33 (bs, 9H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-3ffdafc446224883987985de4b088e93
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Linked notes

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