{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester → {1-[4-(7-Amino-8-hydroxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037379Notes

Reaction equation

HRID 1037379 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15](C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].I[C:38]1[C:43](=[O:44])[C:42]2[CH:45]=[CH:46][C:47]3[N:48]=C[O:50][C:51]=3[C:41]=2[O:40][C:39]=1[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:38]3[C:43](=[O:44])[C:42]4[C:41](=[C:51]([OH:50])[C:47]([NH2:48])=[CH:46][CH:45]=4)[O:40][C:39]=3[C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 67067635{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 670680127-Iodo-8-phenyl-chromeno[7,8-d]oxazol-6-one

Product 1

HCID 67067987{1-[4-(7-Amino-8-hydroxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 14%

Procedure

Following the procedure used to prepare {1-[4-(6-fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester, 7-iodo-8-phenyl-chromeno[7,8-d]oxazol-6-one was reacted to give the title compound as a yellow oil (25 mg, 14%). LCMS (Method G): RT=3.75 min, [M+H]+=499.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-498860300a434d94a046846145d98693
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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