2-(Isocyanatomethyl)furan → 1-{(1S,2R)-2-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-1-methyl-2-phenylethyl}-3-(2-furylmethyl)urea

HRID 1098886Notes

Reaction equation

HRID 1098886 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:19]([CH3:21])[NH2:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][N:34]=[C:35]=[O:36]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C@@H:19]([NH:20][C:35]([NH:34][CH2:33][C:29]4[O:28][CH:32]=[CH:31][CH:30]=4)=[O:36])[CH3:21])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 42238112-(Isocyanatomethyl)furanHCID 59339817(alphaS,betaR)-beta-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-alpha-methylbenzeneethanamine

Product 1

HCID 593396411-{(1S,2R)-2-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-1-methyl-2-phenylethyl}-3-(2-furylmethyl)ureaYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(αS,βR)-β-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-α-methylbenzeneethanamine (100 mg, 0.28 mmol), as described in Example 1, is dissolved in 1.77 mL dichloromethane and furylmethylisocyanate (34.1 mg, 0.28 mmol) is dropwise added. After stirring for 45 min at r.t. the solvent is removed and the residue purified by chromatography (silicagel, eluents: hexane/ethylacetate). 116.2 mg (86.7%) of the title compound are obtained.

Workup

  1. customis removed
  2. customthe residue purified by chromatography (silicagel, eluents: hexane/ethylacetate)

Sources & evidence

ORD record
ord-576a58b3db1642a58cb50695549f5e84
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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