Cyanoacetamide → Carboxyamidotriazole

HRID 388758Notes

Reaction equation

HRID 388758 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:21])[C:11]=1[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH2:5][N:6]=[N+:7]=[N-:8].[C:22]([CH2:24][C:25]([NH2:27])=[O:26])#[N:23]>>[CH:18]1[C:13]([C:12]([C:11]2[C:2]([Cl:1])=[CH:3][C:4]([CH2:5][N:6]3[N:7]=[N:8][C:24]([C:25]([NH2:27])=[O:26])=[C:22]3[NH2:23])=[CH:9][C:10]=2[Cl:21])=[O:20])=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=1

Participants

3

Reactant 2

HCID 7898CyanoacetamideHCID 136496623,5-Dichloro-4-(4-chlorobenzoyl)benzyl azide

Product 1

HCID 108144Carboxyamidotriazole

Procedure

After protection of the alcohol group in 3,5-dichlorobenzyl alcohol, as the TBDMS ether step (step 1), the ether is reacted with 4 chlorobenzoyl chloride to form the substituted benzophene (step 2). The benzophene is treated with thionyl chloride (step 3) and then with sodium azide (step 4) to form 3,5-dichloro-4-(4-chlorobenzoyl)benzyl azide. Reaction of this azide with cyanoacetamide produces L651582 (step 5). Reaction of L651582 with orotic acid forms the L651582 orotate (2:1) (step 6).

Sources & evidence

ORD record
ord-e029852b691b448a99cd709d91e456ae
Source dataset
uspto-grants-2013_02
Patent number
US08377973B2

Reaction notes

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