4-Phenoxyphenyl isocyanate → N-(4-phenoxyphenyl)-N'-[2-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-yl]urea

HRID 1825826Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][C:13]([NH2:17])=[CH:14]3)=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:18]([C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[O:18]([C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32]([NH:17][C:13]2[CH:12]=[CH:11][C:10]3[C:15](=[CH:16][N:8]([CH2:7][CH2:6][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[N:9]=3)[CH:14]=2)=[O:33])=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-(2-pyrrolidin-1-yl-ethyl)-2H-indazol-5-ylamine (0.100 g, 0.434 mmol), 4-phenoxyphenyl isocyanate (0.0917 g, 0.434 mmol) and 6 mL of THF was stirred at 50° C. for 1 hour. The mixture was cooled to room temperature and the solvents removed under vacuo. The resultant solid was triturated in ether and collected by filtration to provide the titled product. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.66 (m, 4 H), 2.50 (m, 4 H), 2.96 (m, 2 H), 4.48 (t, J=5.93 Hz, 2 H), 6.97 (m, 4 H), 7.11 (m, 2 H), 7.36 (m, 2 H), 7.50 (m, 3 H), 7.88 (m, 1 H), 8.26 (s, 1 H), 8.54 (s, 1 H), 8.64 (s, 1 H); MS (DCI/NH3) m/z 441 [M+H]+.

Workup

temperatureThe mixture was cooled to room temperature
customthe solvents removed under vacuo
customThe resultant solid was triturated in ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-05013dde2d334a7d867db3ffa72d21f0
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049307B2

Reaction notes

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