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

HRID 33466

反応式

HRID 33466 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1a84642e03924887bbc708307d7190b0
出典データセット
uspto-grants-2008_09
特許番号
US07429603B2

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