1H-Indazol-6-amine → HCID 44467390, compound

HRID 2281395Notes

Reaction equation

HRID 2281395 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH:10]1[CH2:18][CH2:17][CH2:16][CH:12]([C:13]([NH2:15])=[O:14])[CH2:11]1.CCN(C(C)C)C(C)C.[NH2:28][C:29]1[CH:37]=[C:36]2[C:32]([CH:33]=[N:34][NH:35]2)=[CH:31][CH:30]=1>CC#N.C(O)CCC>[NH:35]1[C:36]2[C:32](=[CH:31][CH:30]=[C:29]([NH:28][C:2]3[N:7]=[C:6]([N:10]4[CH2:18][CH2:17][CH2:16][CH:12]([C:13]([NH2:15])=[O:14])[CH2:11]4)[C:5]([F:9])=[CH:4][N:3]=3)[CH:37]=2)[CH:33]=[N:34]1

Participants

7

Reactant 4

HCID 814231H-Indazol-6-amineHCID 81531DiisopropylethylamineHCID 929803-PiperidinecarboxamideHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 44467390HCID 44467390, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-dichloro-5-fluoropyrimidine (167 mg, 1.00 mmol), nipecotamide (128 mg, 1.00 mmol) and DIEA (0.350 mL, 2.01 mmol) in CH3CN (4 mL) was stirred at room temperature for 20 h. It was concentrated in vacuo. The residue was dissolved in nBuOH (4 mL). 2 mL of the nBuOH solution was taken, to which 6-aminoindazole (100 mg, 0.75 mmol) was added. The solution was stirred at 116° C. for 6 h. nBuOH was removed in vacuo. The residue was purified by HPLC to give the titled compound (63 mg). MS 356.3 (M+H); UV 206.8, 249.8, 276.8, 291.8 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. dissolutionThe residue was dissolved in nBuOH (4 mL)
  3. additionwas added
  4. customwas removed in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-e546b74cc4474459831c764c087746cb
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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