Tetrahydrofuran → 1-{3-[(3-amino-1H-indazol-4-yl)ethynyl]phenyl}-3-(2-fluoro-5-methylphenyl)urea

HRID 589915Notes

Reaction equation

HRID 589915 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12]([NH2:19])=[N:13][NH:14]3)[CH:5]=[CH:6][CH:7]=1.[F:20][C:21]1[CH:26]=[C:25](C)[CH:24]=[CH:23][C:22]=1[N:28]=[C:29]=[O:30].O1CCC[CH2:32]1>>[NH2:19][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[CH:18][C:10]=2[C:9]#[C:8][C:4]2[CH:3]=[C:2]([NH:1][C:29]([NH:28][C:22]3[CH:23]=[C:24]([CH3:32])[CH:25]=[CH:26][C:21]=3[F:20])=[O:30])[CH:7]=[CH:6][CH:5]=2)[NH:14][N:13]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 542290432-Fluoro-1-isocyanato-4-methylbenzeneHCID 1186384254-((3-aminophenyl)ethynyl)-1H-indazol-3-amine2×

Product 1

HCID 1186384371-{3-[(3-amino-1H-indazol-4-yl)ethynyl]phenyl}-3-(2-fluoro-5-methylphenyl)urea

Procedure

4-((3-aminophenyl)ethynyl)-1H-indazol-3-amine (50 mg, 0.2 mmol) was taken in 2 ml of tetrahydrofuran, reaction was set under nitrogen atmosphere. 2-fluoro-1-isocyanato-4-methylbenzene was taken in 1 ml of tetrahydrofuran and added dropwise to the solution of 4-((3-aminophenyl)ethynyl)-1H-indazol-3-amine in tetrahydrofuran. The reaction was stirred at room temperature for 30 min, loaded onto silica and columned to give 1-{3-[(3-amino-1H-indazol-4-yl)ethynyl]phenyl}-3-(2-fluoro-5-methylphenyl)urea.

Workup

  1. customreaction

Sources & evidence

ORD record
ord-dde2bb6c0ee9408883e2ad7ec53643b1
Source dataset
uspto-grants-2016_01
Patent number
US09233968B1

Reaction notes

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