Diisopropylethylamine → HCID 118390030, compound

HRID 1477966Notes

Reaction equation

HRID 1477966 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)[CH:5]=[CH:4][N:3]=1.[CH3:26][N:27]1[CH:31]=[C:30]([NH2:32])[CH:29]=[N:28]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:26][N:27]1[CH:31]=[C:30]([NH:32][C:2]2[N:7]=[C:6]([NH:8][CH:9]3[CH2:10][CH2:11][C:12]4([CH2:16][N:15]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:14][CH2:13]4)[CH2:24][CH2:25]3)[CH:5]=[CH:4][N:3]=2)[CH:29]=[N:28]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 47709901-methyl-1H-pyrazol-4-amineHCID 118390099HCID 118390099, compound

Product 1

HCID 118390030HCID 118390030, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of tert-butyl 8-((2-chloropyrimidin-4-yl)amino)-2-azaspiro[4.5]decane-2-carboxylate (0.4 g, 1.09 mmol) and 1-methyl-1H-pyrazol-4-amine (0.16 g, 1.64 mmol) in n-BuOH (5 mL) was added DIPEA (0.28 g, 2.18 mmol). The mixture was stirred at 150° C. for 16 h then concentrated in vacuo and the residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the product as a red solid (0.51 g, 98%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1)

Sources & evidence

ORD record
ord-c9ad5567786f4f1a8614f949f11213fc
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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