Triethylamine → 5-bromo-N-(2-piperidin-1-ylphenyl)furan-2-carboxamide

HRID 33466노트

반응식

HRID 33466 반응식
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[N:10]1([C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[NH2:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:10]1([C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[NH:18][C:7]([C:5]2[O:6][C:2]([Br:1])=[CH:3][CH:4]=2)=[O:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

참가 물질

8

반응물 6

HCID 8471TriethylamineHCID 685115-Bromo-2-furanecarboxylic acidHCID 4587952-(Piperidin-1-yl)anilineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 8891325-bromo-N-(2-piperidin-1-ylphenyl)furan-2-carboxamide수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 5-bromofuroic acid (Aldrich) (1.0 mmol), 2-piperdinoaniline (1.0 mmol), 1-hydroxybenzotriazole hydrate (“HOBT”) (1.2 mmol), and triethylamine (“Et3N”) (2 mmol) in DCM (10 mL) was stirred for 10 min at room temperature. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (“EDCI”) (1.2 mmol) was then added and the resulting orange solution was stirred overnight. The reaction mixture was treated with saturated sodium bicarbonate (“NaHCO3”) solution (10 mL) and extracted with DCM. The combined organic layers were dried over MgSO4, and concentrated under reduced pressure to afford the crude product as an orange solid. Purification by silica gel chromatography afforded the pure yellow product in 85% yield. MS: 349 (M+1). 1H NMR (CDCl3, 300 MHz): δ 9.75 (br s, 1H), 8.45 (d, 1H), 7.22-7.05 (m, 4H), 6.50 (d, 1H), 3.00-2.80 (m, 4H), 1.95-1.80 (m, 4H), 1.75-1.60 (m, 2H).

후처리

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1a84642e03924887bbc708307d7190b0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429603B2

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