Sodium Carbonate → Tert-butyl 4-((2-(pyridin-4-yl)ethyl)carbamoyl)piperidine-1-carboxylate

HRID 83654

反応式

HRID 83654 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:19]([CH:23]([CH3:25])C)[CH:20]([CH3:22])C.C1C=[CH:28][C:29]2N(O)N=[N:32][C:30]=2C=1.N1C=CC=CC=1CCN.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.C(Cl)CCl>[N:19]1[CH:20]=[CH:22][C:28]([CH2:29][CH2:30][NH:32][C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])=[CH:25][CH:23]=1

参加物

8

反応物 5

HCID 10340Sodium CarbonateHCID 757711-HydroxybenzotriazoleHCID 759192-PyridineethanamineHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

生成物 1

HCID 68379709Tert-butyl 4-((2-(pyridin-4-yl)ethyl)carbamoyl)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

The following was added to DCM: 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (600 mg, 2.62 mmol), DIPEA (1.37 mL, 7.85 mmol), EDC (552 mg, 2.88 mL), HOBT (441 mg, 2.88 mmol), and pyridylethylamine (0.34 mL, 2.88 mL). The solution was stirred at rt for 17 h, at which time the DCM was stripped off and 10% aq. sodium carbonate was added. Material was extracted out with EtOAc (3×). The organic extractions were pooled, dried over magnesium sulfate, and concentrated in vacuo. The residue was taken up in a small amount of EtOAc and diethyl ether was added. The precipitate was collected over a filter and washed with diethyl ether to give the title compound as an off-white solid. (Yield: 634 mg, 1.9 mmol, 73%) 1H NMR (400 MHz, CDCl3) 8.49, 7.09, 5.67-5.54, 4.10, 3.52, 2.81, 2.68, 2.14, 1.81-1.66, 1.56, 1.43

後処理

  1. extractionMaterial was extracted out with EtOAc (3×)
  2. extractionThe organic extractions
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. additionwas added
  6. customThe precipitate was collected over
  7. filtrationa filter
  8. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-846faa964a934afb9aae8f248cc6860c
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

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