Cyanoacetic acid → HCID 15136415, compound

HRID 1638332Notes

Reaction equation

HRID 1638332 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-e91d08e46b2f4c9f909d870c53270aea
Source dataset
uspto-grants-1989_11
Patent number
US04879296

Reaction notes

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