1-(Tetrahydro-2H-pyran-4-YL)-1H-pyrazol-4-amine → HCID 71667334, compound

HRID 1481254Notes

Reaction equation

HRID 1481254 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[N:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[O:18]1[CH2:23][CH2:22][CH:21]([N:24]2[CH:28]=[C:27]([NH2:29])[CH:26]=[N:25]2)[CH2:20][CH2:19]1>COCCO>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[C:6]3[N:7]=[C:2]([NH:29][C:27]4[CH:26]=[N:25][N:24]([CH:21]5[CH2:22][CH2:23][O:18][CH2:19][CH2:20]5)[CH:28]=4)[N:3]=[CH:4][C:5]=3[N:10]=[N:9]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 510637031-(Tetrahydro-2H-pyran-4-YL)-1H-pyrazol-4-amineHCID 89719373HCID 89719373, compound

Product 1

HCID 71667334HCID 71667334, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 74.9 mg (0.30 mmol) 5-chloro-3-(4-fluoro-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and 60.2 mg (0.36 mmol) 1-(tetrahydro-pyran-4-yl)-1H-pyrazol-4-ylamine in 0.5 ml 2-methoxy-ethanol is stirred for 4 hours at 90° C. The reaction mixture is cooled to room temperature. The solvent is partially removed under vacuum and the residue is purified by preparative HPLC yielding “A20” as brown amorphous solid; HPLC/MS (B): 2.1 min, [M+H] 381;

Workup

  1. customThe solvent is partially removed under vacuum
  2. customthe residue is purified by preparative HPLC
  3. customyielding “A20” as brown amorphous solid
  4. custom2.1 min, [M+H] 381

Sources & evidence

ORD record
ord-6107d433d88f4c9ebb387c6039eae9b4
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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