{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester → (1-{4-[7-(2-Hydroxy-ethyl)-4,8-dioxo-2-phenyl-7,8-dihydro-4H-pyrano[2,3-c]pyridin-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037262Notes

Reaction equation

HRID 1037262 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].[OH:37][CH2:38][CH2:39][N:40]1[CH:45]=[CH:44][C:43]2[C:46](=[O:57])[C:47](I)=[C:48]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[O:49][C:42]=2[C:41]1=[O:58]>>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:47]3[C:46](=[O:57])[C:43]4[CH:44]=[CH:45][N:40]([CH2:39][CH2:38][OH:37])[C:41](=[O:58])[C:42]=4[O:49][C:48]=3[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=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 866710347-(2-Hydroxy-ethyl)-3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione

Product 1

HCID 86671035(1-{4-[7-(2-Hydroxy-ethyl)-4,8-dioxo-2-phenyl-7,8-dihydro-4H-pyrano[2,3-c]pyridin-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl esterYield 96%

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-(2-hydroxy-ethyl)-3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione was reacted to give the title compound (56 mg, 96%) as a colourless solid. LCMS (Method A): RT=4.41 min, [M+H]+=529.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-2ec20058b4c3408d9becd8d43322f3d4
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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