5-Methylfuran-2-carbonyl chloride → HCID 59631242, compound

HRID 1431686Notes

Reaction equation

HRID 1431686 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:26]=1)=[C:5]([CH3:19])[C:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[N:7]2.[CH3:33][C:34]1[O:38][C:37]([C:39](Cl)=[O:40])=[CH:36][CH:35]=1>>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:26]=1)=[C:5]([CH3:19])[C:6]([N:13]1[CH2:14][CH2:15][N:16]([C:39]([C:37]3[O:38][C:34]([CH3:33])=[CH:35][CH:36]=3)=[O:40])[CH2:17][CH2:18]1)=[N:7]2

Participants

3

Reactant 2

HCID 27598515-Methylfuran-2-carbonyl chlorideHCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

Product 1

HCID 59631242HCID 59631242, compound

Procedure

Prepared according to Procedure R using 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine (50.0 mg, 0.11 mmol) and 5-methylfuran-2-carbonyl chloride to give (4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazin-1-yl)(5-methylfuran-2-yl)methanone. 1H NMR (CDCl3) δ ppm 2.11 (br s, 3H), 2.49 (br s, 3H), 3.06 (t, J=5.6 Hz, 4H), 3.30-3.40 (m, 4H), 3.69 (t, J=5.6 Hz, 4H), 3.86 (br s, 4H), 6.27 (br s, 1H), 6.52 (s, 1H), 6.94 (d, J=3.2 Hz, 1H), 7.16 (s, 1H), 7.28-7.31 (m, 1H), 7.53 (br s, 1H,), 7.79 (br s, 1H), 8.37 (s, 1H). Mass Spectrum (ESI) m/e=549.0 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-06becfef960d4c26b9a9e190322c5195
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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