{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester → 3-[4-(1-Amino-cyclobutyl)-phenyl]-7-(2-methoxy-ethyl)-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione

HRID 1037230Notes

Reaction equation

HRID 1037230 reaction equation
C(OC(=O)[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)(C)(C)C.I[C:38]1[C:39](=[O:59])[C:40]2[CH:45]=[CH:44][N:43]([CH2:46][CH2:47][O:48][CH3:49])[C:42](=[O:50])[C:41]=2[O:51][C:52]=1[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>>[NH2:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:38]3[C:39](=[O:59])[C:40]4[CH:45]=[CH:44][N:43]([CH2:46][CH2:47][O:48][CH3:49])[C:42](=[O:50])[C:41]=4[O:51][C:52]=3[C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1

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 866710183-Iodo-7-(2-methoxy-ethyl)-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione

Product 1

HCID 510295893-[4-(1-Amino-cyclobutyl)-phenyl]-7-(2-methoxy-ethyl)-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dioneYield 100%

Procedure

(1-{4-[7-(2-Methoxy-ethyl)-4,8-dioxo-2-phenyl-7,8-dihydro-4H-pyrano[2,3-c]pyridin-3-yl]-phenyl}-carbamic acid tert-butyl ester: 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, 3-iodo-7-(2-methoxy-ethyl)-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione was reacted to give the title compound as a colourless oil (82 mg, 100%). LCMS (Method B): RT=4.63 min, [M+H]+=543.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-788e7aa3250f407b8fd6eae0abff3cae
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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