Triethylamine → HCID 66958605, compound

HRID 1360532Notes

Reaction equation

HRID 1360532 reaction equation
Cl[C:2](=[N:9][OH:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:11]([C:16]1[N:17]([CH2:44][CH2:45][CH3:46])[N:18]=[C:19]2[C:28]=1[C:27]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:21]=[C:20]2[N:29]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:12][CH2:13][C:14]#[CH:15].C(N(CC)CC)C>ClCCl>[C:3]1([C:2]2[CH:15]=[C:14]([CH2:13][CH2:12][CH2:11][C:16]3[N:17]([CH2:44][CH2:45][CH3:46])[N:18]=[C:19]4[C:28]=3[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[C:20]4[N:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:37]([O:39][C:40]([CH3:42])([CH3:43])[CH3:41])=[O:38])[O:10][N:9]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756315N-hydroxybenzenecarboximidoyl chloride2×HCID 86604924HCID 86604924, compound

Product 1

HCID 66958605HCID 66958605, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

α-Chlorobenzaldoxime (0.64 g, 4.1 mmol) was added to a solution of di(tert-butyl) 1-pent-4-ynyl-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate (prepared as described in Parts A-E of Example 57, 1.36 g, 2.76 mmol) and triethylamine (0.60 mL, 4.14 mmol) in dichloromethane (10 mL). The solution was heated at 40° C. for 19 hours, during which time additional α-chlorobenzaldoxime (0.65 g) was added. The reaction was worked up as described in Part B of Example 595. The crude product was purified by chromatography (silica gel, sequential elution with 20% then 40% ethyl acetate in hexanes) to provide 1.35 g of di(tert-butyl) 1-[3-(3-phenylisoxazol-5-yl)propyl]-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate as a white solid.

Workup

  1. additionwas added
  2. customThe crude product was purified by chromatography (
  3. washsilica gel, sequential elution with 20%

Sources & evidence

ORD record
ord-f928401680fe4dbfa80a302c069a4899
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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