3-Pyridineacetic acid, hydrochloride (1:1) → 4-(3-(N-t-butyloxycarbonyl-N-methylamino)propanoylamino)-1-benzyl-5-imidazole carboxamide

HRID 382395Notes

Reaction equation

HRID 382395 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]=1[C:7]([NH2:9])=[O:8].[C:17]([O:21][C:22]([N:24]([CH2:26][CH2:27][C:28](O)=[O:29])[CH3:25])=[O:23])([CH3:20])([CH3:19])[CH3:18].Cl.N1C=CC=C(CC(O)=O)C=1>>[C:17]([O:21][C:22]([N:24]([CH2:26][CH2:27][C:28]([NH:1][C:2]1[N:3]=[CH:4][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]=1[C:7]([NH2:9])=[O:8])=[O:29])[CH3:25])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 27609523-(Methylamino)propanoic acid, N-BOC protectedHCID 140006201-benzyl-4-amino-1H-imidazole-5-carboxamide

Product 1

HCID 183601794-(3-(N-t-butyloxycarbonyl-N-methylamino)propanoylamino)-1-benzyl-5-imidazole carboxamideYield 72%

Procedure

An amidation reaction and post-treatment were carried out under the same conditions as in Example 17, using 1.92 g (8.96 mmol) of 4-amino-1-benzyl-5-imidazolecarboxamide which was prepared in the same manner as in Reference Example 2 and 3-(N-t-butyloxycarbonyl-N-methylamino)propionic acid, instead of 3-pyridylacetic acid hydrochloride, to obtain 2.56 g of 4-(3-(N-t-butyloxycarbonyl-N-methylamino)propanoylamino)-1-benzyl-5-imidazole carboxamide (yield 72%).

Workup

  1. customAn amidation reaction

Sources & evidence

ORD record
ord-0e35a30f0acc412187e8f039f1731b5f
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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