Cyanoacetic acid → HCID 15136415, compound

HRID 703117Notes

Reaction equation

HRID 703117 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.BrCC1C(C#N)=CC=CC=1.[CH3:21][N:22]=[C:23]=[O:24].[C:25]([CH2:27][C:28]([OH:30])=O)#[N:26]>>[NH2:26][C:25]1[N:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([C:2]#[N:1])=[CH:4][CH:5]=2)[C:23](=[O:24])[N:22]([CH3:21])[C:28](=[O:30])[CH:27]=1

Participants

5

Reactant 4

HCID 9740Cyanoacetic acidHCID 12228Methyl IsocyanateHCID 826084-(Aminomethyl)benzonitrileHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 15136415HCID 15136415, compound

Procedure

α-Amino-p-tolunitrile (prepared from α-bromotolunitrile in a modification of the method described by J. H. Short and T. D. Darby, J. Med. Chem., 10 (5), 833, 1967) was treated first with methyl isocyanate followed by cyanoacetic acid according to the method of V. Papesch and E. F. Schroeder (J. Org. Chem., 1951, 16, 1879) to yield 4-[(6-amino-1,2,3,4-tetrahydro-3-methyl-2,4-dioxo-1-pyrimidinyl)methyl]benzonitrile, which was then nitrosated, reduced, and condensed with 4-formylcinnamic acid following an analogous procedure to that of Example 3 to give the title compound as a yellow solid with a melting point greater than 350° C. Analysis for (C23H17N5O4): C,64.63; H,4.01; N,16.38. Found: C,64.58; H,4.06; N,16.36.

Sources & evidence

ORD record
ord-015ece393d574fc48ecf2f669f89aace
Source dataset
uspto-grants-1991_01
Patent number
US04981857

Reaction notes

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