Dimethylformamide → 1-benzyl-4-amino-1H-imidazole-5-carboxamide

HRID 382375

반응식

HRID 382375 반응식
C([N:3]([CH2:6]C)CC)C.ON1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2N=N1.Cl.CN(C)CCC[N:24]=[C:25]=[N:26]CC.Cl.N1C=CC=C(CC(O)=[O:39])C=1.[CH3:41][N:42]([CH3:45])[CH:43]=O>>[NH2:24][C:25]1[N:26]=[CH:43][N:42]([CH2:45][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:41]=1[C:6]([NH2:3])=[O:39]

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 140006201-benzyl-4-amino-1H-imidazole-5-carboxamide

실험 절차

1.4 ml (10 mmol) of triethylamine, 1.5 g (11 mmol) of 1-hydroxybenzotriazole, and 2.3 g (12 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added to a solution of 1.7 g (10 mmol) of 3-pyridylacetic acid hydrochloride in 100 ml of N,N-dimethylformamide under cooling with ice. The mixture was stirred for one hour while cooling with ice. 2.05 g (9.5 mmol) of 4-amino-1-benzyl-5-imidazole carboxamide which was obtained in Reference Example 2 was added to the reaction solution, followed by stirring overnight. The reaction solution was concentrated under vacuum and 5% aqueous solution of sodium hydrogencarbonate was added to the concentrate to deposite a solid precipitate. The precipitate was collected by filtration through a funnel with a glass filter. The resulting solid was washed with 5% aqueous solution of sodium hydrogencarbonate, then with distilled water, and dried under vacuum to obtain a crude product, which was recrystallized from hot methanol to obtain 1.83 g of 1-benzyl-4-(3-pyridylacetylamino)-5-imidazolecarboxamide (yield 57%).

후처리

  1. temperatureunder cooling with ice
  2. temperaturewhile cooling with ice

출처 및 근거

ORD 기록
ord-2c9bfec1a42b4d28806880a5b9e3285c
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310070B1

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