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

HRID 2068555
ノート
印刷プレビュー

反応式

HRID 2068555 の反応式
[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.[C:16]([O:20][C:21]([NH:23][C:24]1([C:27](O)=[O:28])[CH2:26][CH2:25]1)=[O:22])([CH3:19])([CH3:18])[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:27]([C:24]3([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:26][CH2:25]3)=[O:28])[C:4]2=[N:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58304055(R)-5,6-Dihydro-4H-benzo[F]imidazo[1,2-A]azepin-4-amine

生成物 1

HCID 67234396
Tert-butyl N-[1-[[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamoyl]cyclopropyl]carbamate
収率 79%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Combine (4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine (570 mg, 2.86 mmol), 1-(tert-butoxycarbonylamino)cyclopropanecarboxylic acid (commercially available, 633.19 mg, 3.15 mmol), 1-hydroxybenzotriazole (464 mg, 3.43 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (658 mg; 3.43 mmol) in tetrahydrofuran (10 mL). Add diisopropylethylamine (599 μL, 3.43 mmol) and stir the reaction for approximately 16 hours at ambient temperature under nitrogen. Dilute the reaction with ethyl acetate, wash with dilute 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 85% EtOAc/hexanes) to give the title compound (860 mg, 79%) as a white solid: MS (m/z): 383 (M+1).

後処理

  1. customthe reaction for approximately 16 hours at ambient temperature under nitrogen
  2. additionDilute
  3. washwash with dilute 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 85% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-f81b889126af49dda6873b0babf6a856
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299061B2

反応ノート

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