Ethylamine → HCID 71575824, compound

HRID 1050868Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20]([C:22]3[C:23](=[O:36])[N:24]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[CH:25]=[CH:26][C:27]=3I)=[O:21])=[C:14]([F:37])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[CH2:38]([NH2:40])[CH3:39]>>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20]([C:22]3[C:23](=[O:36])[N:24]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[CH:25]=[CH:26][C:27]=3[NH:40][CH2:38][CH3:39])=[O:21])=[C:14]([F:37])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 6341Ethylamine

HCID 86703363HCID 86703363, compound

Product 1

HCID 71575824HCID 71575824, compoundYield 76.9%

Procedure

Using the procedure of Example 7, 1-(4-fluoro-phenyl)-4-iodo-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid [4-(2-acetylamino-pyridin-4-yloxy)-2,5-difluoro-phenyl]-amide (90 mg, 0.145 mmol) and a methanolic solution of ethylamine (10 mL) were combined to afford N-(4-((2-acetamidopyridin-4-yl)oxy)-2,5-difluorophenyl)-4-(ethylamino)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (60 mg, 76.9% yield). 1H NMR (400 MHz, DMSO-d6): δ 13.23 (s, 1 H), 10.58 (s, 1 H), 10.49 (m, 1 H), 8.47 (dd, J=12.9, 7.2 Hz, 1 H), 8.18 (d, J=5.8 Hz, 1 H), 7.70 (d, J=7.9 Hz, 1 H), 7.65 (m, 1 H), 7.52 (dd, J=11.2, 7.4 Hz, 1 H), 7.47 (m, 2 H), 7.34 (m, 2 H), 6.70 (dd, J=5.8, 2.5 Hz, 1 H), 6.28 (d, J=7.9 Hz, 1 H), 3.42 (m, 2 H), 2.03 (s, 3 H), 1.24 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 538.0 (M+H).

Sources & evidence

ORD record: ord-d2f6263a9c4940e09c04960eb8bb456e
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09387202B2

Reaction notes

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