Ethyl 3-bromopropionate → Ethyl 3-[9-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate

HRID 1514247노트

반응식

HRID 1514247 반응식
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][NH:24][CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH:6]=[N:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11].C(N(CC)C(C)C)(C)C.Br[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>C(#N)C>[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][N:24]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH:6]=[N:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11]

참가 물질

5

반응물 3

HCID 68320Ethyl 3-bromopropionate2회HCID 81531Diisopropylethylamine2회HCID 684690769-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride

생성물 1

HCID 59403487Ethyl 3-[9-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate수율 30.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

To a solution of 9-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride (Preparation 90) (80 mg, 0.189 mmol) in acetonitrile (10 ml) was added N,N-diisopropylethylamine (0.066 ml, 0.378 mmol) followed by ethyl 3-bromopropanoate (0.048 ml, 0.378 mmol). The reaction mixture was heated at 80° C. overnight. A further 1 equivalent of N,N-diisopropylethylamine and ethyl 3-bromopropanoate were added and heating continued overnight. The reaction mixture was cooled and evaporated. The residue was purified by column chromatography on silica. Elution with 40-60% ethyl acetate in cyclohexane to give the title compound as an olive green coloured oil (28 mg).

후처리

  1. temperatureheating continued overnight
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica
  5. washElution with 40-60% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-bf6b27dfdb5b4259b980e3138beeeda9
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222245B2

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