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3-[4-(1-amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-7-carboxylic acid amide → {1-[4-(6-Carbamoyl-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butylester

HRID 1037179
Notes
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Reaction equation

HRID 1037179 reaction equation
NC1(C2C=CC(C3C(=O)C4C(=CC([C:23]([NH2:25])=[O:24])=CC=4)OC=3C3C=CC=CC=3)=CC=2)CCC1.[C:32]([O:36][C:37](=[O:69])[NH:38][C:39]1([C:43]2[CH:48]=[CH:47][C:46]([C:49]3[C:58](=[O:59])[C:57]4[C:52](=[CH:53][C:54]([O:61][CH3:62])=[C:55](Br)[CH:56]=4)[O:51][C:50]=3[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)=[CH:45][CH:44]=2)[CH2:42][CH2:41][CH2:40]1)([CH3:35])([CH3:34])[CH3:33]>>[C:32]([O:36][C:37](=[O:69])[NH:38][C:39]1([C:43]2[CH:48]=[CH:47][C:46]([C:49]3[C:58](=[O:59])[C:57]4[C:52](=[CH:53][C:54]([O:61][CH3:62])=[C:55]([C:23](=[O:24])[NH2:25])[CH:56]=4)[O:51][C:50]=3[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)=[CH:45][CH:44]=2)[CH2:42][CH2:41][CH2:40]1)([CH3:35])([CH3:34])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 510309713-[4-(1-amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-7-carboxylic acid amideHCID 67067774{1-[4-(6-bromo-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 67067752{1-[4-(6-Carbamoyl-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butylesterYield 37%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-7-carboxylic acid amide, {1-[4-(6-bromo-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (115 mg, 0.20 mmol) was reacted to give the title compound (40 mg, 37%). LCMS (Method B): RT=4.58 min, [M+H]+=541.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-06cd106ae870477abeeedc7b5ad3b0b3
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546376B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes