1-Butanol → HCID 44468088, compound

HRID 2281384Notes

Reaction equation

HRID 2281384 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.C([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])C.[NH2:17][C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[N:23][NH:24]2)=[CH:20][CH:19]=1.C(O)CCC.[CH3:32][C:33]#[N:34]>>[NH2:34][CH2:33][CH:32]1[CH2:14][CH2:13][N:12]([C:6]2[C:5]([F:9])=[CH:4][N:3]=[C:2]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([CH:22]=[N:23][NH:24]4)=[CH:20][CH:19]=3)[N:7]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 5

HCID 2631-ButanolHCID 6342AcetonitrileHCID 8471TriethylamineHCID 814231H-Indazol-6-amineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 44468088HCID 44468088, compound

Procedure

A mixture of 2,4-dichloro-5-fluoropyrimidine (167 mg, 1.00 mmol), 4-N-Boc-aminomethyl piperidine (214 mg, 1.00 mmol) and triethylamine (0.300 mL, 2.15 mmol) in CH3CN (4 mL) was stirred at room temperature for 20 h. It was concentrated in vacuo. The residue was dissolved in nBuOH (6 mL). 2 mL of the nBuOH solution was taken, to which 6-aminoindazole (66 mg, 0.49 mmol) was added. The solution was stirred at 116° C. for 20 h. nBuOH was removed in vacuo. The residue was dissolved in TFA (2 mL). After being stirred at room temperature for 2 h, TFA was removed in vacuo. The residue was purified by HPLC to give the titled compound (40 mg). MS 342.5 (M+H); UV 205.8, 246.8, 276.8 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. dissolutionThe residue was dissolved in nBuOH (6 mL)
  3. additionwas added
  4. customwas removed in vacuo
  5. dissolutionThe residue was dissolved in TFA (2 mL)
  6. stirringAfter being stirred at room temperature for 2 h
  7. customTFA was removed in vacuo
  8. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-4cc78086a072445d84200bd9c18ad00e
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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