3-Amino-5-methylisoxazole → cyclobutylmethyl-{1,3-dimethyl-5-[(5-methyl-isoxazol-3-ylamino)-methyl]-1H-pyrazolo[3,4-b]pyridin-6-yl}-ethyl-amine

HRID 577763Notes

Reaction equation

HRID 577763 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[CH:8]1([CH2:12][N:13]([CH2:27][CH3:28])[C:14]2[N:19]=[C:18]3[N:20]([CH3:24])[N:21]=[C:22]([CH3:23])[C:17]3=[CH:16][C:15]=2[CH:25]=O)[CH2:11][CH2:10][CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[CH:8]1([CH2:12][N:13]([C:14]2[N:19]=[C:18]3[N:20]([CH3:24])[N:21]=[C:22]([CH3:23])[C:17]3=[CH:16][C:15]=2[CH2:25][NH:7][C:4]2[CH:3]=[C:2]([CH3:1])[O:6][N:5]=2)[CH2:27][CH3:28])[CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 661723-Amino-5-methylisoxazoleHCID 5049666Sodium triacetoxyborohydrideHCID 574444326-(cyclobutylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

Product 1

HCID 58689766cyclobutylmethyl-{1,3-dimethyl-5-[(5-methyl-isoxazol-3-ylamino)-methyl]-1H-pyrazolo[3,4-b]pyridin-6-yl}-ethyl-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

5-Methyl-isoxazol-3-ylamine (0.37 g, 3.8 mmol) was added to a solution of 6-(cyclobutylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (0.54 g, 1.9 mmol) in anhydrous chloroform (20 mL) and acetic acid (0.2 mL) under nitrogen. After stirring for 15 min at RT, sodium triacetoxyborohydride (1.20 g, 5.7 mmol) was added slowly and this mixture was stirred at RT overnight. After evaporation of chloroform in vacuo, water (30 mL) and ethyl acetate (30 mL) were added to the residue. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated to give title compound, which was taken on without further purification.

Workup

  1. stirringthis mixture was stirred at RT overnight
  2. customAfter evaporation of chloroform in vacuo, water (30 mL) and ethyl acetate (30 mL)
  3. additionwere added to the residue
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-198d36cbb7a0484d8d8572c385980cab
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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