{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester → HCID 67067733, compound

HRID 1037356Notes

Reaction equation

HRID 1037356 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[C:24](F)[CH:25]=4)[O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH:37][CH2:38][CH2:39][N:40]1C2=C3C(=CC=C2[CH:42]=[N:41]1)C(=O)C(I)=C(C1C=CC=CC=1)O3.OCCN1N=C2C3OC(C4C=CC=CC=4)=C(I)C(=O)C=3C=CC2=C1>>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21]([O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:22]3[N:40]([CH2:39][CH2:38][OH:37])[N:41]=[CH:42][C:23]3=[CH:24][CH:25]=4)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 67067635{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 67067805HCID 67067805, compoundHCID 67067862HCID 67067862, compound

Product 1

HCID 67067733HCID 67067733, compoundYield 37%

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, the crude mixture of 1-(2-hydroxy-ethyl)-7-iodo-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one and 2-(2-hydroxy-ethyl)-7-iodo-8-phenyl-2H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one was reacted to give (1-{4-[1-(2-hydroxy-ethyl)-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester (53.3 mg, 37%), LCMS (Method H): RT=3.86 min, [M+H]+=552, as the earlier eluted compound and (1-{4-[2-(2-hydroxy-ethyl)-6-oxo-8-phenyl-2,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester (57.1 mg, 40%), LCMS (Method H): RT=3.68 min, [M+H]+=552, as the later eluted compound.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-d326d6638e33413c8f91344d99612b66
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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