Diisopropylethylamine → HCID 86680153, compound

HRID 1915955Notes

Reaction equation

HRID 1915955 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]1[C:14]2([CH2:19][NH:18][CH2:17][CH2:16][CH2:15]2)[CH2:13][N:12]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].CCN(C(C)C)C(C)C>C(O)CCC>[CH3:7][N:6]1[C:2]([N:18]2[CH2:17][CH2:16][CH2:15][C:14]3([CH2:11][N:12]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:13]3)[CH2:19]2)=[C:3]([N+:8]([O-:10])=[O:9])[CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazoleHCID 44182345tert-Butyl 2,6-diazaspiro[3.5]nonane-2-carboxylate

Product 1

HCID 86680153HCID 86680153, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

5-Chloro-1-methyl-4-nitro-pyrazole (0.16 g; 0.99 mmol) and tert-butyl 2,8-diazaspiro[3.5]nonane-2-carboxylate (0.2 g, 0.88 mmol) were suspended in butan-1-ol (2 mL), followed by the addition of DIPEA (0.7 mL; 3.9616 mmol). The reaction mixture was heated at 120° C. for 2 days. Evaporated all solvent and purified the crude mixture by silica gel eluting with a gradient of 0-30% ethyl acetate in dichloromethane. Tert-butyl 6-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,6-diazaspiro[3.5]nonane-2-carboxylate (200 mg) was obtained a yellow oil in a 57% yield. MS (ESI) m/z: 352.2 [M+H+].

Workup

  1. customEvaporated all solvent
  2. custompurified the crude mixture by silica gel eluting with a gradient of 0-30% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-b50cde1f4ebc492ba9ed361ef6f99d1f
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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