2-Amino-5-(diethylamino)toluene → HCID 59713614, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([N:14]=[C:15]=[S:16])[N:8]=[C:7]([C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)[C:6]=2[CH:27]=1.[CH2:28]([N:30]([CH2:39][CH3:40])[C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[C:33]([CH3:38])[CH:32]=1)[CH3:29]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([NH:14][C:15]([NH:37][C:34]3[CH:35]=[CH:36][C:31]([N:30]([CH2:39][CH3:40])[CH2:28][CH3:29])=[CH:32][C:33]=3[CH3:38])=[S:16])[N:8]=[C:7]([C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)[C:6]=2[CH:27]=1Participants
Conditions
- Temperature
- 70 °C
Procedure
As illustrated in the scheme above, a solution of 7-chloro-5-(2,4-dimethoxy-5-pyrimidinyl)-1,3-dihydro-3-isothiocyanato-1-methyl-2H-1,4-benzodiazepin-2-one (0.069 g, 0.146 mmol) and N4,N4-diethyl-2-methyl-1,4benzenediamine (0.029 g, 0.161 mmol) in (CH2Cl)2 (5.0 mL) was heated at 70° C. for 16 h. The reaction was cooled and concentrated in vacuo, and the residue was purified by silica gel column chromatography (7:3 CH2Cl2:EtOAc) to provide the title compound as a light orange solid (0.074 g, 87%). 1H-NMR (CDCl3): δ 8.64 (s, 1H), 7.52 (dd, J=2.5 Hz, J=8.8 Hz, 1H), 7.40 (s, 1H), 7.35 (d, J=7.8 Hz, 1H), 7.32 (d, J=9.0 Hz, 1H), 7.20 (d, J=2.2 Hz, 1H), 7.17-7.13 (m, 1H), 6.54-6.51 (m, 2H), 6.06 (d, J=8.0 Hz, 1H), 4.05 (s, 3H), 3.74 (s, 3H), 3.42 (s, 3H), 3.40-3.27 (m, 4H), 2.30 (s, 3H), 1.17 (t, J=7.1 Hz, 6H). HRMS calculated for (C28H32ClN7O3S+H) (M+H)+: 582.2054. Found (ESI): 582.2076.
Workup
- temperatureThe reaction was cooled
- concentrationconcentrated in vacuo
- customthe residue was purified by silica gel column chromatography (7:3 CH2Cl2:EtOAc)
Sources & evidence
- ORD record
- ord-6cc0f349f1c74ab9aec89f0430c759bc
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375101B2
Reaction notes
Loading…