Triethylamine → Tert-butyl 3-(2-(benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)piperidine-1-carboxylate

HRID 502544ノート

反応式

HRID 502544 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH2:13])=[N:2]1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([C:27](O)=[O:28])[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH:13][C:27]([CH:23]2[CH2:24][CH2:25][CH2:26][N:21]([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[CH2:22]2)=[O:28])=[N:2]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 16768374N1-(benzo[d]isothiazol-3-yl)ethane-1,2-diamine

生成物 1

HCID 11854495Tert-butyl 3-(2-(benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of N1-(benzo[d]isothiazol-3-yl)ethane-1,2-diamine (600 mg, 3.11 mmol), 1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (854 mg, 3.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (585 mg, 3.7 mmol) and triethylamine (577 μL, 3.7 mmol) in dichloromethane (40 mL) was allowed to stir at room temperature overnight. The reaction mixture was washed successively with 1N aqueous hydrochloric acid, saturated sodium bicarbonate solution and water, then dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure. Purification by flash column chromatography, on silica gel, eluting with a mixture of 25% ethyl acetate in hexanes gave fractions that were combined and concentrated under reduced pressure to yield tert-butyl 3-(2-(benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)piperidine-1-carboxylate as a white solid, (325 mg). 1H NMR (300 MHz, DMSO-d6): 8.1 (m, 2H), 7.92 (m, 3H), 7.9 (d, 1H), 7.5 (m, 1H), 7.3 (m, 1H), 3.9 (m, 2H), 3.5 (m, 2H), 3.3 (m, 2H), 2.8 (m, 2H), 2.2 (m, 1H), 1.8 (m, 1H), 1.6 (m, 3H), 1.3 ppm (s, 9H). MW=405 confirmed by LC-MS, tr=3.81 min (Method B) MH+=406.

後処理

  1. washThe reaction mixture was washed successively with 1N aqueous hydrochloric acid, saturated sodium bicarbonate solution and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customPurification by flash column chromatography
  6. washon silica gel, eluting with a mixture of 25% ethyl acetate in hexanes
  7. customgave fractions that
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-5e4034dc2ee34719adfc155f90dd7663
出典データセット
uspto-grants-2010_08
特許番号
US07776847B2

反応ノート

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