4-Phenoxyphenyl isocyanate → HCID 11419337, compound

HRID 1790110Notes

Reaction equation

HRID 1790110 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH2:17])[CH:14]=3)[NH: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:14]=[C:15]3[C:16](=[CH:11][CH:12]=2)[N:8]([CH2:7][CH2:6][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[N:9]=[CH:10]3)=[O:33])=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 27348964-Phenoxyphenyl isocyanateHCID 69652762HCID 69652762, compound

Product 1

HCID 11419337HCID 11419337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine (0.100 g, 0.434 mmol) and 4-phenoxyphenyl isocyanate (0.0917 g, 0.434 mmol) in 6 mL of THF was stirred at 50° C. for 1 hour, cooled to room temperature and concentrated under reduced pressure. The residue was triturated in diethyl ether and collected by filtration to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.63 (m, 4 H), 2.44 (m, J=6.44 Hz, 4 H), 2.86 (t, J=6.61 Hz, 2 H), 4.46 (t, J=6.78 Hz, 2 H), 6.97 (m, 4 H), 7.09 (m, 1 H), 7.35 (m, 3 H), 7.49 (m, 2 H), 7.59 (m, 1 H), 7.88 (m, 1 H), 7.96 (s, 1 H), 8.65 (m, 2 H); MS (ESI) m/z 442 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated in diethyl ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5ee0f7c74eb045949bb2ca2b5cb79163
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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