Diisopropylethylamine → HCID 118390068, compound

HRID 1478023Notes

Reaction equation

HRID 1478023 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:27])[CH:9]2[CH2:26][CH2:25][C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH2:11][CH2:10]2)[C:5]([Cl:28])=[CH:4][N:3]=1.Cl.[CH3:30][N:31]1[CH:35]=[C:34]([NH2:36])[CH:33]=[N:32]1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:28][C:5]1[C:6]([N:8]([CH3:27])[CH:9]2[CH2:26][CH2:25][C:12]3([CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:16][CH2:17]3)[CH2:11][CH2:10]2)=[N:7][C:2]([NH:36][C:34]2[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 173542681-methyl-1H-pyrazol-4-amineHCID 118390056HCID 118390056, compound

Product 1

HCID 118390068HCID 118390068, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of tert-butyl 9-((2,5-dichloropyrimidin-4-yl)(methyl)amino)-3-azaspiro[5.5]undecane-3-carboxylate (241 mg, 0.56 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (172.32 mg, 1.29 mmol) in butan-1-ol (5 mL) was added DIPEA (217.14 mg, 1.68 mmol). The reaction mixture was stirred at 150° C. in a sealed tube overnight, then cooled down to rt, and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=100/1 to 10/1) to give the title compound as a white solid (198 mg, 72%).

Workup

  1. temperaturecooled down to rt
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=100/1 to 10/1)

Sources & evidence

ORD record
ord-6459739d5bc94b929ab7ac3a90b1ba4b
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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