p-Toluenesulfonic acid → HCID 178463003, compound

HRID 923347Notes

Reaction equation

HRID 923347 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([NH2:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25](=O)[CH2:26][C:27](OCC)=[O:28])=[CH:22][CH:23]=2)[CH:18]=[N:17]1)[CH3:15].CC1C=CC(S(O)(=O)=O)=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]3[NH:13][C:11]4[N:10]([N:9]=[C:8]([C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=5)[N:12]=4)[C:27](=[O:28])[CH:26]=3)=[CH:22][CH:23]=2)[CH:18]=[N:17]1)[CH3:15]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 90109086ethyl 3-(1-ethyl-1H-indazol-5-yl)-3-oxopropanoateHCID 1785082995-(4-fluorophenyl)-4H-1,2,4-triazol-3-amine

Product 1

HCID 178463003HCID 178463003, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

To a solution of 3-(4-fluorophenyl)-1H-1,2,4-triazol-5-amine (100 mg, 0.56 mmol) in diphenyl ether (1 ml) was added ethyl 3-(1-ethyl-1H-indazol-5-yl)-3-oxopropanoate (400 mg, 1.540 mmol) and TsOH (6 mg, 0.03 mmol), and the resulting mixture was strirred for 2.5 h at 170° C. The reaction mixture was then quenched by the addition of ethyl ether (8 ml). The solids were collected by filtration and washed with dichloromethane (5 ml) to afford 5-(1-ethyl-1H-indazol-5-yl)-2-(4-fluorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a light yellow solid (69 mg, 24%).

Workup

  1. customThe reaction mixture was then quenched by the addition of ethyl ether (8 ml)
  2. filtrationThe solids were collected by filtration
  3. washwashed with dichloromethane (5 ml)

Sources & evidence

ORD record
ord-42c90e75eb5b45c9b2968eb767854450
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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