1-(5-Methyl-1,2-oxazol-3-yl)methanamine → 7-(3,5-Dimethyl-4-isoxazolyl)-4-{[(5-methyl-3-isoxazolyl)methyl]amino}-6-(methyloxy)-3-quinolinecarboxamide

HRID 1043001Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:21]([NH2:23])=[O:22].[CH3:24][C:25]1[O:29][N:28]=[C:27]([CH2:30][NH2:31])[CH:26]=1>C(O)CCC>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:31][CH2:30][C:27]4[CH:26]=[C:25]([CH3:24])[O:29][N:28]=4)=[C:3]([C:21]([NH2:23])=[O:22])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-quinolinecarboxamide (for a preparation see Intermediate 56, 331 mg) and [(5-methyl-3-isoxazolyl)methyl]amine (2.5 eq) in butanol (20 ml) was heated to 110° C. for 4 h. The reaction mixture was evaporated to dryness and hydrolysed with water. The mixture was extracted with DCM and the organic dried over Na2SO4, filtered and concentrated to dryness (280 mg). Used without purification in the subsequent reaction (Example 52).

Workup

customThe reaction mixture was evaporated to dryness and hydrolysed with water
extractionThe mixture was extracted with DCM
dry with materialthe organic dried over Na2SO4
filtrationfiltered
concentrationconcentrated to dryness (280 mg)
customUsed without purification
customin the subsequent reaction (Example 52)

Sources & evidence

ORD record: ord-2d581f10179841f9abc9d2d0236c3e52
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557984B2

Reaction notes

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