Ethylamine → HCID 86270238, compound

HRID 1472620Notes

Reaction equation

HRID 1472620 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[C:5]([F:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1[C:26](=[O:39])[N:27]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH:28]=[CH:29][C:30]=1I)=[O:24].[CH2:40]([NH2:42])[CH3:41]>>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[C:5]([F:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1[C:26](=[O:39])[N:27]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH:28]=[CH:29][C:30]=1[NH:42][CH2:40][CH3:41])=[O:24]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 90447769HCID 90447769, compound

Product 1

HCID 86270238HCID 86270238, compoundYield 34%

Procedure

A mixture of Example A5 (100 mg, 0.155 mmol) in a methanolic solution of ethylamine (10 mL) was heated at 80° C. for 3 h. The mixture was concentrated to dryness and purified by HPLC to afford N-(2,5-difluoro-4-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)phenyl)-4-(ethylamino)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (30 mg, 34%). 1H-NMR (400 MHz, DMSO-d6): δ 13.29 (s, 1H), 10.51 (t, J=5.2 Hz, 1H), 8.52 (m, 1H), 8.47 (d, J=6.0 Hz, 1H), 8.40 (s, 1H), 8.10 (s, 1H), 7.72 (d, J=8.0 Hz, 1H), 7.59 (dd, J=7.6, 11.2 Hz, 1H), 7.50 (d, J=5.2 Hz, 2H), 7.39 (m, 3H), 6.92 (d, J=4.4 Hz, 1H), 6.30 (d, J=8.0 Hz, 1H), 3.88 (s, 3H), 3.48 (m, 2H; obscured by water), 1.26 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 561.2 (M+H+).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-f3b6c7eda9af4c5b8eeebcdbc9c3e015
Source dataset
uspto-grants-2015_04
Patent number
US09012635B2

Reaction notes

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