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1-Hydroxybenzotriazole → N-[1-[[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamoyl]cyclopropyl]-4-ethoxy-benzamide

HRID 2068552
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HRID 2068552 반응식
[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[CH2:8][CH2:9][C@@H:10]([NH2:11])[C:4]2=[N:3][CH:2]=1.[CH2:16]([O:18][C:19]1[CH:33]=[CH:32][C:22]([C:23]([NH:25][C:26]2([C:29](O)=[O:30])[CH2:28][CH2:27]2)=[O:24])=[CH:21][CH:20]=1)[CH3:17].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>O1CCCC1.C(OCC)(=O)C>[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[CH2:8][CH2:9][C@@H:10]([NH:11][C:29]([C:26]3([NH:25][C:23](=[O:24])[C:22]4[CH:32]=[CH:33][C:19]([O:18][CH2:16][CH3:17])=[CH:20][CH:21]=4)[CH2:28][CH2:27]3)=[O:30])[C:4]2=[N:3][CH:2]=1
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참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58304055(R)-5,6-Dihydro-4H-benzo[F]imidazo[1,2-A]azepin-4-amineHCID 583041121-[(4-Ethoxybenzoyl)amino]cyclopropanecarboxylic acid

생성물 1

HCID 53242014
N-[1-[[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamoyl]cyclopropyl]-4-ethoxy-benzamide
수율 80%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Combine (4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine (0.50 g, 2.51 mmol), 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylic acid (0.75 mg, 3.01 mmol), 1-hydroxybenzotriazole (407 mg, 3.01 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (577 mg, 3.01 mmol) in tetrahydrofuran (40 mL). Add diisopropylethylamine (0.53 mL, 3.01 mmol) and stir the reaction for approximately 16 hours at ambient temperature under nitrogen. Dilute the reaction with ethyl acetate, wash with saturated sodium bicarbonate and brine, dry over sodium sulfate, and concentrate the organic layer under reduced pressure. Purify the residue by flash chromatography (25% EtOAc/hexanes to 100% EtOAc) to give the title compound (860 mg, 80%): MS (m/z): 431 (M+1).

후처리

  1. customthe reaction for approximately 16 hours at ambient temperature under nitrogen
  2. additionDilute
  3. washwash with saturated sodium bicarbonate and brine
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate the organic layer under reduced pressure
  6. customPurify the residue by flash chromatography (25% EtOAc/hexanes to 100% EtOAc)

출처 및 근거

ORD 기록
ord-4fdd762286d8416ca940233eae1294b2
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08299061B2

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