4-Chloro-2-[(ethoxycarbonyl)amino]benzonitrile → HCID 18367734, compound

HRID 379875Notes

Reaction equation

HRID 379875 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([NH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=1.Br[CH2:17][C:18]([C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=1)=[O:19]>>[NH2:7][C:6]1[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:9][CH:8]=2)[N:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:17]=1[C:18]([C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=1)=[O:19]

Participants

3

Reactant 2

HCID 183678884-Chloro-2-[(ethoxycarbonyl)amino]benzonitrileHCID 230032102-Bromo-1-(3-methylpyridin-2-yl)ethan-1-one

Product 1

HCID 18367734HCID 18367734, compound

Procedure

The title compound was prepared according to the procedure described in step 2 of Example 1 from 4-chloro-2-(ethoxycarbonylamino)benzonitrile (Example 1, step 1) and 2-bromoacetyl-3-methylpyridine (step 1). 1H-NMR (CDCl3) δ: 8.36 (1 H, dd, J=1.1, 4.8 Hz), 8.14 (1 H, d, J=1.8 Hz), 7.64 (1 H, ddd, J=0.7, 1.5, 7.0 Hz), 7.51 (1 H, dd, J=0.7, 8.4 Hz), 7.24 (1 H, d, J=1.8, 8.8 Hz), 7.22 (1 H, d, J=7.7 Hz), 6.05 (2 H, br s), 3.78 (2 H, q, J=7.3 Hz), 2.63 (3 H, s), 1.01 (3 H, t, J=7.3 Hz).

Sources & evidence

ORD record
ord-77df9044886e495ba0f0239ba2731b3d
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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