1,2-Dichloroethane → HCID 136337175, compound

HRID 1428850Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

Titanium (IV) chloride (1.2 mL, 11 mmol) was carefully added to a solution of 1-[(2,3-dihydro-benzo[1,4]dioxin-5-ylimino)-ethoxycarbonylamino-methyl]-1H-pyrazole-4-carboxylic acid ethyl ester (1.39 g, 3.58 mmol) and DCE (11 mL), and the resulting solution was heated to 110° C. for 2 h. The reaction mixture was cooled to room temperature and ethanol (60 mL) was added. The resulting slurry was stirred at room temperature for 30 min; the precipitate was then collected to yield the titled compound (0.970 g, 78% yield). MS (ESI/Cl): mass calcd. for C16H14N4O6, 342.1; m/z found, 343.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.78 (s, 1H), 8.90 (d, J=0.5 Hz, 1H), 8.31 (s, 1H), 7.62 (d, J=8.7 Hz, 1H), 7.06 (d, J=8.8 Hz, 1H), 4.48-4.35 (m, 4H), 4.30 (q, J=7.1 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H).

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe precipitate was then collected

Sources & evidence

ORD record: ord-7fa2446f603a49108d935feedd5b77de
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937078B2

Reaction notes

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