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Triethylamine → N-[3(R,S)-5-Cycloheptyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]N'-[3-(N-methyl-N'-piperazinyl)phenyl]urea

HRID 743712
ノート
印刷プレビュー

反応式

HRID 743712 の反応式
C1([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]([CH3:19])[C:11](=[O:20])[CH:10]([NH:21][C:22]([O:24]C3C=CC([N+]([O-])=O)=CC=3)=O)[N:9]=2)CCCCCC1.C(N([CH2:39][CH3:40])CC)C.[NH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([N:48]2[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]2)[CH:43]=1>CN(C)C=O>[CH2:40]1[CH2:39][CH2:17][CH:18]([C:10]2([NH:21][C:22]([NH:41][C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([N:48]4[CH2:49][CH2:50][N:51]([CH3:54])[CH2:52][CH2:53]4)[CH:43]=3)=[O:24])[N:9]=[CH:8][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]([CH3:19])[C:11]2=[O:20])[CH2:13][CH2:14][CH2:8]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 194246105-Cycloheptyl-1,3-dihydro-1-methyl-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one

生成物 1

HCID 131719557N-[3(R,S)-5-Cycloheptyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]N'-[3-(N-methyl-N'-piperazinyl)phenyl]urea

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

反応条件

温度
50 °C

実験手順

To a stirred solution of 5-cycloheptyl-1,3-dihydro-1-methyl-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (200 mg) in anhydrous dimethylformamide (5 ml), under an atmosphere of nitrogen, was added triethylamine (61 μl). After 2 min a solution of 1-amino-3-(N-methyl-N'-piperazinyl)benzene (85 mg) in anhydrous dimethylformamide (5 ml) was added and the solution heated at 50° C. for 1.5 h. After this time the solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (20 ml) and water (20 ml). An undissolved solid was filtered off and triturated with anhydrous diethyl ether to give the desired urea (128 mg) as a white solid. 1H NMR (360 MHz, D6 -DMSO) δ 1.13-1.94 (12H, m), 2.19 (3H, s), 2.40-2.43 (4H, m), 3.03-3.12 (5H, m), 3.30 (3H, s), 5.04 (1H, d, J=8.4 Hz), 6.49 (1H, dd, 8.1 and 1 Hz), 6.62 (1H, d, J=9.0 Hz), 7.03 (1H, t, J=8.1 Hz), 7.12 (1H, m), 7.22 (1H, d, J=8.4 Hz), 7.38 (1H, dd, J=7.6 and 7.6 Hz), 7.54 (1H, d, J=7.7 Hz), 7.63 (1H, dd, J=8.3 and 8.3 Hz), 7.76 (1H, d, J=7.6 Hz), 8.86 (1H, s). MS (CI, NH3) 502 (M+).

後処理

  1. customAfter this time the solvent was evaporated in vacuo
  2. customthe residue partitioned between ethyl acetate (20 ml) and water (20 ml)
  3. filtrationAn undissolved solid was filtered off
  4. customtriturated with anhydrous diethyl ether

出典と根拠

ORDレコード
ord-7c4998ecaf564c68a8fc224c68ab9619
出典データセット
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05556969

反応ノート

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