4-Phenoxyphenyl isocyanate → HCID 11235379, compound

HRID 1825823Notes

Reaction equation

HRID 1825823 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([NH2:14])=[CH:11]2)=[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[CH:13]=[C:12]2[C:7]([CH: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]2)=[N:6]1

Participants

4

Reactant 2

HCID 27348964-Phenoxyphenyl isocyanateHCID 22138917HCID 22138917, compound

Product 1

HCID 11235379HCID 11235379, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(2-dimethylamino-ethyl)-2H-indazol-5-ylamine (42.0 mg, 0.206 mmol), 4-phenoxyphenyl isocyanate (43.4 mg, 0.206 mmol) and 2 mL of THF, was stirred at 50° C. for 6 hours. The solvents were removed under vacuo, the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethylsulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) ppm 2.56 (s, 8H), 4.66 (m, 2H), 6.95–7.38 (m, 10H), 7.56 (m, 1H), 7.93 (m, 1H), 8.3 (s, 1H), 8.75 (m, 2H); MS (DCI/NH3) m/z 416 [M+H]+.

Workup

  1. customThe solvents were removed under vacuo
  2. dissolutionthe residue was dissolved in 1.5 mL of a 1:1 mixture of dimethylsulfoxide/methanol
  3. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-98ca4228959942cd9af4e9ed7869c93e
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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