Aniline → HCID 71584707, compound

HRID 1257243Notes

Reaction equation

HRID 1257243 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:20]3[C:21]([F:37])=[CH:22][C:23]([F:36])=[C:24]([NH:26][C:27](=[O:35])OC4C=CC=CC=4)[CH:25]=3)[C:13](=[O:19])[N:14]2[CH2:17][CH3:18])=[CH:9][N:8]=1)=[O:5])#[N:2].[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CS(C)=O>[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:20]3[CH:25]=[C:24]([NH:26][C:27]([NH:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:35])[C:23]([F:36])=[CH:22][C:21]=3[F:37])[C:13](=[O:19])[N:14]2[CH2:17][CH3:18])=[CH:9][N:8]=1)=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 6115AnilineHCID 86713671HCID 86713671, compound

Product 1

HCID 71584707HCID 71584707, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of phenyl (5-(7-(2-cyanoacetamido)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)carbamate (400 mg, 0.80 mmol) and aniline (158 mg, 1.6 mmol) in DMSO (3 mL) was heated at 60° C. overnight and purified via reverse-phase chromatography (MeCN/H2O with 0.1% TFA) to afford 2-cyano-N-(3-(2,4-difluoro-5-(3-phenylureido)phenyl)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)acetamide (50 mg, 13% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.23 (s, 1H), 8.92 (s, 1H), 8.78 (s, 1H), 8.20-8.16 (m, 2H), 8.11 (s, 1H),7.49-7.39 (m, 4H), 7.29-7.25 (m, 2H), 6.96 (t, J=7.2 Hz, 1H) 4.26-4.21 (q, J=6.8 Hz, 2H), 4.09 (s, 2H),1.30-1.26 (t, J=6.8 Hz, 3H); MS (ESI) m/z: 503.2 [M+H]+.

Workup

  1. custompurified via reverse-phase chromatography (MeCN/H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-cf54526057b04b3d86334c432327073e
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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