1,2-Dichloroethane → HCID 136337161, compound

HRID 1428824Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11](=[N:30][C:31]([O:33]CC)=O)[NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[CH:10]=1)=[O:5])[CH3:2].ClCCCl>[Ti](Cl)(Cl)(Cl)Cl.CCO>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:30][C:31](=[O:33])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:22][CH:21]=4)[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Titanium (IV) chloride (0.86 mL, 7.8 mmol) was added to a solution of 1-{ethoxycarbonylimino-[4-(naphthalen-1-yloxy)-phenylamino]methyl}-1H-pyrazole-4-carboxylic acid ethyl ester (0.74 g, 1.6 mmol) and DCE (10 mL), and the resulting mixture was heated to 90° C. for 16 h. The reaction mixture was cooled to room temperature and poured into 50 mL EtOH. The mixture was stirred for 30 min and the solid precipitate was collected by vacuum filtration (0.46 g, 69%). MS (ESI): mass calcd. for C24H18N4O4, 426.1; m/z found, 427.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.87 (s, 1H), 8.99 (s, 1H), 8.29 (s, 1H), 8.05 (d, J=7.5 Hz, 1H), 8.02 (d, J=8.3 Hz, 1H), 7.86 (d, J=8.3 Hz, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.70 (dd, J=8.9, 2.9 Hz, 1H), 7.64-7.60 (m, 1H), 7.60-7.53 (m, 2H), 7.39 (d, J=2.8 Hz, 1H), 7.23 (d, J=7.4 Hz, 1H), 4.30 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 3H).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationthe solid precipitate was collected by vacuum filtration (0.46 g, 69%)

Sources & evidence

ORD record: ord-b801f5e286044d34b07c043e15c3e475
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937078B2

Reaction notes

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