1,2-Dichloroethane → 2-(Morpholin-4-yl)acetamide

HRID 334936

반응식

HRID 334936 반응식
C(Cl)CCl.C1C=CC2N(O)N=[N:11]C=2C=1.[N:15]1([CH2:21][C:22]([OH:24])=O)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(N(CC)CC)C>CN(C=O)C>[N:15]1([CH2:21][C:22]([NH2:11])=[O:24])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

참가 물질

6

반응물 4

HCID 111,2-Dichloroethane2회HCID 8471Triethylamine2회HCID 757711-Hydroxybenzotriazole2회HCID 4389684-Morpholineacetic acid2회

생성물 1

HCID 6679102-(Morpholin-4-yl)acetamide수율 108.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of [5-(3-amino-ethoxy)-1,3-dihydro-isoindol-2-yl]-(2,4-dihydroxy-5-isopropyl-phenyl)-methanone hydrochloride (100 mg, 0.255 mmoles) in DMF (10 ml) was added EDC (59 mg, 0.306 mmoles), HOBt (41 mg, 0.306 mmoles), morpholin-4-yl-acetic acid (37 mg, 0.255 mmoles) and triethylamine (43 μl, 0.306 mmoles) and stirred at ambient temperature for one hour. To the reaction mixture was added further EDC (20 mg, 0.104 mmoles), HOBt (14 mg, 0.104 mmoles), morpholin-4-yl-acetic acid (12 mg, 0.083 mmoles) and triethylamine (14 μl, 0.100 mmoles) and stirred at ambient temperature for a further 2 hours. Solvent removed in vacuo. The residue was purified by flash chromatography [Biotage SP4: 25S, flow rate 25 ml/min, gradient 20% DMAW 90 in DCM to 100% DMAW 90] and then by preparative HPLC to give N-{2-[2,4-dihydroxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindol-5-yloxy]-ethyl}-2-morpholin-4-yl-acetamide as a colourless viscous oil (40 mg, 33%). 1H NMR (Me-d3-OD) 7.20 (1H, br s); 7.18 (1H, s); 6.90 (2H, br m); 6.40 (1H, s); 4.10 (2H, t); 3.73 (4H, m); 3.63 (2H, t); 3.20 (1H, m); 3.18 (2H, s); 2.60 (4H, m); 1.25 (6H, d). MS: [M+H]+ 484.

후처리

  1. stirringstirred at ambient temperature for a further 2 hours
  2. customSolvent removed in vacuo
  3. customThe residue was purified by flash chromatography [Biotage SP4: 25S, flow rate 25 ml/min, gradient 20% DMAW 90 in DCM to 100% DMAW 90]

출처 및 근거

ORD 기록
ord-d19c5f2f25764f9b9f545bc67bf0a229
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883790B2

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