Triethylamine → HCID 131719555, compound

HRID 743705Notes

Reaction equation

HRID 743705 reaction equation
C1([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:11](=[O:23])[CH:10]([NH:24][C:25]([O:27]C3C=CC([N+]([O-])=O)=CC=3)=O)[N:9]=2)CCCCCC1.C(N([CH2:42][CH3:43])CC)C.[NH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([N:51]2[CH2:56][CH2:55][N:54]([CH3:57])[CH2:53][CH2:52]2)[CH:46]=1>CN(C)C=O>[CH2:43]1[CH2:42][CH2:17][CH:18]([C:10]2([NH:24][C:25]([NH:44][C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([N:51]4[CH2:52][CH2:53][N:54]([CH3:57])[CH2:55][CH2:56]4)[CH:46]=3)=[O:27])[N:9]=[CH:8][C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:11]2=[O:23])[CH2:13][CH2:14][CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 19424605HCID 19424605, compound

Product 1

HCID 131719555HCID 131719555, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 5-cycloheptyl-1,3-dihydro-1-(2-methylpropyl)-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (150 mg) in anhydrous dimethylformamide (3 ml), under an atmosphere of nitrogen, was added triethylamine (42 μl). After 5 min a solution of 1-amino-3-(N-methyl-N'-piperazinyl)benzene (64 mg) in anhydrous dimethylformamide (2 ml) was added and the solution heated at 50° C. for 1 h. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (20 ml) and water (20 ml). The undissolved solid was filtered off, washed with ethyl acetate and water, then triturated with anhydrous diethyl ether to yield the desired urea (87 mg) as a white solid. 1H NMR (360 MHz, D6 -DMSO) δ 0.66 (3H, d, J=6.6 Hz), 0.77 (3H, d, J=6.6 Hz), 1.20-1.80 (12H, m), 1.96-2.10 (1H, m), 2.20 (3H, s), 2.18-2.20 (4H, m), 3.03-3.05 (4H, m), 3.14-3.18 (1H, m), 3.62 (1H, dd, J=13.9 and 4.4 Hz), 4.13 (1H, dd, J=13.9 and 9.6 Hz), 5.00 (1H, d, J=8.5 Hz), 6.49 (1H, d, J=8.3 Hz), 6.61 (1H, d, J=7.7 Hz), 7.03 (1H, t, J=8.1 Hz), 7.11 (1H, m), 7.23 (1H, d, J=7.7 Hz), 7.37 (1H, dd, J=7 and 7 Hz), 7.59-7.68 (2H, m), 7.78 (1H, d, J=6.8 Hz), 8.84 (1H, s). MS (FAB) 545 (M+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between ethyl acetate (20 ml) and water (20 ml)
  3. filtrationThe undissolved solid was filtered off
  4. washwashed with ethyl acetate and water
  5. customtriturated with anhydrous diethyl ether

Sources & evidence

ORD record
ord-792afaa73271439aadac1b94016bbafa
Source dataset
uspto-grants-1996_09
Patent number
US05556969

Reaction notes

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