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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
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HRID 743712 반응식
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
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참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

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온도
50 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-7c4998ecaf564c68a8fc224c68ab9619
출처 데이터셋
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05556969

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