Tributylamine → HCID 178516967, compound

HRID 877045Notes

Reaction equation

HRID 877045 reaction equation
[C:1]1([CH:7]([C:13]([O:15]CC)=O)[C:8]([O:10]CC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][N:23]=[C:22]2[NH2:28].C(N(CCCC)CCCC)CCC.[OH-].[Na+]>O>[F:18][C:19]1[CH:27]=[CH:26][C:25]2[C:21](=[C:22]3[N:28]=[C:8]([OH:10])[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[C:13]([OH:15])[N:23]3[N:24]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 7622TributylamineHCID 14798Sodium HydroxideHCID 66514Diethyl phenylmalonateHCID 43278965-fluoro-1H-indazol-3-amine

Product 1

HCID 178516967HCID 178516967, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

14.3 g (60.2 mmol) Diethyl phenylmalonate, 9.1 g (60.2 mol) 5-fluoro-1H-indazol-3-ylamine and 25.3 mL tributyl amine were heated for 15 h at 180° C. The reaction mixture was treated with 2M sodium hydroxide and water and extracted with tert-butyl methyl ether. The organic phase was discarded and the aqueous phase was acidified with conc. hydrochloric acid. The precipitate was collected by filtration and washed with water to obtain 14 g of the desired product which is 90% pure. MS (Cl, M+1): 296

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-82062a891e66482fa740c1cc84f880d7
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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