3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(1-Amino-cyclobutyl)-phenyl]-8-difluoromethoxy-2-phenyl-pyrano[2,3-c]pyridin-4-one

HRID 1037234Notes

Reaction equation

HRID 1037234 reaction equation
NC1(C2C=CC(C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=CC=2)CCC1.C(OC(=O)[NH:36][C:37]1([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:48](=[O:67])[C:49]4[C:50]([O:59][C:60]=3[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[C:51]([O:55][CH:56]([F:58])[F:57])[N:52]=[CH:53][CH:54]=4)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C>>[NH2:36][C:37]1([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:48](=[O:67])[C:49]4[C:50]([O:59][C:60]=3[C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)=[C:51]([O:55][CH:56]([F:57])[F:58])[N:52]=[CH:53][CH:54]=4)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067822{1-[4-(8-Difluoromethoxy-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510295903-[4-(1-Amino-cyclobutyl)-phenyl]-8-difluoromethoxy-2-phenyl-pyrano[2,3-c]pyridin-4-oneYield 46%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(8-difluoromethoxy-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a pale orange solid (9 mg, 46%). 1H NMR (400 MHz, DMSO-d6): δ 8.26 (d, J=5 Hz, 1H), 7.90 (t, J=72 Hz, 1H), 7.80 (d, J=5 Hz, 1H), 7.44-7.35 (m, 7H), 7.16-7.13 (m, 2H), 2.40-2.32 (m, 2H), 2.12-2.04 (m, 2H), 2.04-1.95 (m, 1H), 1.70-1.61 (m, 1H). LCMS (Method E): RT=3.74 min, [M+Na]+=457.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-557243703db64e7abe3196588101ba1f
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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