1,2-Dichloroethane → HCID 136337160, compound

HRID 1428822Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:33])=[C:21]([CH3:34])[CH:20]=2)=[N:12][C:13]([O:15]CC)=O)[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:12][C:13](=[O:15])[C:24]3[C:19](=[CH:20][C:21]([CH3:34])=[C:22]([O:25][C:26]4[C:27]([CH3:33])=[CH:28][CH:29]=[CH:30][C:31]=4[CH3:32])[CH:23]=3)[N:18]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Titanium (IV) chloride (0.25 mL, 2.3 mmol) was added to a solution of 1-{[4-(2,6-dimethyl-phenoxy)-3-methyl-phenylamino]-ethoxycarbonylimino-methyl}-1H-pyrazole-4-carboxylic acid ethyl ester (0.97 g, 2.1 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 concentrated to dryness. The solid was and purified by FCC (CH3CN/DCM, gradient 0:100 to 20:80) to provide the titled compound (0.28 g, 32%). MS (ESI): mass calcd. for C23H22N4O4, 418.4; m/z found, 419.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.77 (s, 1H), 8.96 (s, 1H), 8.28 (s, 1H), 7.69 (s, 1H), 7.25 (d, J=7.4 Hz, 2H), 7.18 (dd, J=8.3, 6.7 Hz, 1H), 6.78 (s, 1H), 4.30 (q, J=7.1 Hz, 2H), 2.55 (s, 3H), 2.08 (s, 6H), 1.32 (t, J=7.1 Hz, 3H).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated to dryness
custompurified by FCC (CH3CN/DCM, gradient 0:100 to 20:80)

Sources & evidence

ORD record: ord-2b7ab25ef08447b091fe256166f39ab9
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937078B2

Reaction notes

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