N-(2-Chloroethylidene)hydroxylamine → di(tert-butyl) 1-[3-(3-methylisoxazol-5-yl)propyl]-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate

HRID 2283880Notes

Reaction equation

HRID 2283880 reaction equation
[CH2:1]([C:6]1[N:7]([CH2:34][CH2:35][CH3:36])[N:8]=[C:9]2[C:18]=1[C:17]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=1[N:11]=[C:10]2[N:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:2][CH2:3][C:4]#[CH:5].Cl[CH2:38][CH:39]=[N:40][OH:41]>>[CH3:38][C:39]1[CH:5]=[C:4]([CH2:3][CH2:2][CH2:1][C:6]2[N:7]([CH2:34][CH2:35][CH3:36])[N:8]=[C:9]3[C:18]=2[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[N:11]=[C:10]3[N:19]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[O:41][N:40]=1

Participants

3

Reactant 2

HCID 57350373N-(2-Chloroethylidene)hydroxylamineHCID 86604925di(tert-butyl) 1-pent-4-ynyl-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate

Product 1

HCID 66958332di(tert-butyl) 1-[3-(3-methylisoxazol-5-yl)propyl]-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonateYield 34.8%

Procedure

Using the method of Example 595 Part B, di(tert-butyl) 1-pent-4-ynyl-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate (4.00 g, 8.05 mmol), prepared as described in Example 615, was reacted with α-chloroacetaldoxime (1.13 g, 12.1 mmol). The crude product was purified by chromatography (silica gel, elution with a gradient of 20-40% ethyl acetate in hexanes) to provide 1.55 g of di(tert-butyl) 1-[3-(3-methylisoxazol-5-yl)propyl]-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate as a glassy solid.

Workup

  1. customprepared
  2. customThe crude product was purified by chromatography (
  3. washsilica gel, elution with a gradient of 20-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-aeaa285f7a4045e7a7af39c4cc4401e8
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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