Diisopropylethylamine → HCID 118389993, compound

HRID 1477978Notes

Reaction equation

HRID 1477978 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:25][CH2:24][C:12]3([CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13]3)[CH2:11][CH2:10]2)[C:5]([CH3:26])=[CH:4][N:3]=1.Cl.[CH3:28][N:29]1[CH:33]=[C:32]([NH2:34])[CH:31]=[N:30]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:26][C:5]1[C:6]([NH:8][CH:9]2[CH2:25][CH2:24][C:12]3([CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13]3)[CH2:11][CH2:10]2)=[N:7][C:2]([NH:34][C:32]2[CH:31]=[N:30][N:29]([CH3:28])[CH:33]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 173542681-methyl-1H-pyrazol-4-amineHCID 118390095HCID 118390095, compound

Product 1

HCID 118389993HCID 118389993, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of tert-butyl 8-((2-chloro-5-methylpyrimidin-4-yl)amino)-2-azaspiro[4.5]decane-2-carboxylate (1.04 g, 2.73 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (365.4 mg, 2.73 mmol) in n-BuOH (8 mL) was added DIPEA (1.06 g, 8.20 mmol) and the reaction mixture was stirred in a sealed tube at 150° C. overnight then concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/100) to give the title compound as yellow oil (1.21 g, 100%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/100)

Sources & evidence

ORD record
ord-213d0b8c1cb94892a746dabb20aedc63
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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