Benzylamine → 4-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid benzylamide

HRID 583769Notes

Reaction equation

HRID 583769 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([NH:20][C:21](=[O:32])[NH:22][C:23]1[CH:24]=[C:25]([C:29]([OH:31])=O)[S:26][C:27]=1[CH3:28])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:33]([NH:40][C:29]([C:25]1[S:26][C:27]([CH3:28])=[C:23]([NH:22][C:21]([NH:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:32])[CH:24]=1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 223425214-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid

Product 1

HCID 103093674-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid benzylamideYield 96.6%

Procedure

The title compound was prepared according to the procedure described for Example 2 using carbonyldiimidazole (0.24 g, 1.7 mmol), 4-(3-benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid from Step 3 (0.27 g, 0.9 mmol), and benzyl amine (0.1 g, 0.9 mmol) to afford 0.33 g of 4-(3-benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid benzylamide. A sample of the crude product was stirred in 2 M aqueous KHCO3 for several hours, filtered off, rinsed with water, dried, and recrystallized from methanol to give product with a mp 180-181° C.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-cc129f83817c43d4bca73631e18acc93
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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