4-Phenoxyphenyl isocyanate → 1-[1-(2-dimethylamino-ethyl)-1H-indazol-5-yl]-3-(4-phenoxy-phenyl)-urea

HRID 1790117Notes

Reaction equation

[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH:7]=[N:6]1.[O:16]([C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:30]([NH:29][C:26]3[CH:27]=[CH:28][C:23]([O:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:24][CH:25]=3)=[O:31])=[CH:11][CH:12]=2)[CH:7]=[N:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1-(2-dimethylamino-ethyl)-1H-indazol-5-ylamine (42 mg, 0.17 mmol), 4-phenoxyphenyl isocyanate (36 mg, 0.17 mmol) in 2 mL of THF was heated to 50° C. for 6 hours, cool to room temperature and concentrated under reduced pressure. The residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) ppm 2.85 (s, 6H), 3.63 (t, J=6.40, 2H), 4.77 (t, J=6.40, 2H), 7.09 (m, 2H), 6.97 (m, 4H), 7.36 (m, 2H), 7.47 (m, 1H), 7.57 (m, 2H), 7.67 (m, 1H), 7.97 (s, 1H), 8.10 (s, 1H), 8.98 (s, 1H); MS (DCI/NH3) m/z 416 [M+H]+.

Workup

temperaturecool to room temperature
concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol
custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-86181e1da498497389831caf81c5c3cb
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071182B2

Reaction notes

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