Diisopropylethylamine → HCID 118390052, compound

HRID 1478019Notes

Reaction equation

HRID 1478019 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]([CH3:28])=[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>[CH3:27][N:8]([C:6]1[C:5]([CH3:28])=[CH:4][N:3]=[C:2]([NH:36][C:34]2[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=2)[N:7]=1)[CH:9]1[CH2:26][CH2:25][C:12]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 173542681-methyl-1H-pyrazol-4-amineHCID 118390023HCID 118390023, compound

Product 1

HCID 118390052HCID 118390052, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of tert-butyl 9-((2-chloro-5-methylpyrimidin-4-yl)(methyl)amino)-3-azaspiro[5.5]undecane-3-carboxylate (211 mg, 0.52 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (160.3 mg, 1.20 mmol) in butan-1-ol (5 mL) was added DIPEA (201.63 mg, 1.56 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 (176.87 mg, 73%).

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-a2b018ffd6fd4c25a80bcf5e253302fe
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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