3-Hydroxy-3-phenyl-1-butyne → HCID 10206059, compound

HRID 351747

Reaction equation

HRID 351747 reaction equation
[C:1]1([C:7](O)([C:9]#[CH:10])C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1[CH:14]=[CH:15][C:16]([C:20]([OH:23])([CH3:22])[CH3:21])=[N+:17]([O-:19])[CH:18]=1.[CH:24]([NH:27][C:28]([C:30]1[C:39](=[O:40])[C:38]2[C:33](=[N:34][CH:35]=[CH:36][CH:37]=2)[N:32](C2C=CC=C(Br)C=2)[CH:31]=1)=[O:29])([CH3:26])[CH3:25]>>[CH:24]1([NH:27][C:28]([C:30]2[C:39](=[O:40])[C:38]3[C:33](=[N:34][CH:35]=[CH:36][CH:37]=3)[N:32]([C:5]3[CH:4]=[CH:3][CH:2]=[C:1]([C:7]#[C:9][C:10]4[CH:18]=[N+:17]([O-:19])[C:16]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:15][CH:14]=4)[CH:6]=3)[CH:31]=2)=[O:29])[CH2:25][CH2:26]1

Participants

4

Reactant 3

HCID 920983-Hydroxy-3-phenyl-1-butyneHCID 129913181-(3-bromophenyl)-N-isopropyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamideHCID 22714291HCID 22714291, compound

Product 1

HCID 10206059HCID 10206059, compound

Procedure

Following the procedure of EXAMPLE 15, but substituting N-cyclopropyl-1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from EXAMPLE 6 for 2-phenyl-3-butyn-2-ol and 5-bromo-2-(1-hydroxy-1-methylethyl)pyridine-N-oxide from present Step 1 for N-isopropyl-1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide, the N-cyclopropyl-1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-3-pyridinylethynyl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide compound was obtained as a solid.

Sources & evidence

ORD record
ord-b91a2ce40fc4409d9fb0abec3b010979
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Linked notes

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