Sodium Hydroxide → HCID 24802808, compound

HRID 1437501Notes

Reaction equation

HRID 1437501 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]2[C:6]([CH:7]([NH2:18])[CH2:8][C:9]3([O:15]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)=[CH:5][CH:4]=1.COC([N:23]1[C:31]2[C:26](=[C:27]([NH:32][C:33](ON3C(=O)CCC3=O)=[O:34])[CH:28]=[CH:29][CH:30]=2)[CH:25]=[N:24]1)=O.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>CN(C)C=O.O.O1CCCC1>[NH:23]1[C:31]2[C:26](=[C:27]([NH:32][C:33]([NH:18][CH:7]3[C:6]4[C:16](=[CH:17][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[O:15][C:9]4([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]4)[CH2:8]3)=[O:34])[CH:28]=[CH:29][CH:30]=2)[CH:25]=[N:24]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 11313556methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylateHCID 24277620HCID 24277620, compound

Product 1

HCID 24802808HCID 24802808, compoundYield 83.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 16C (0.195 g) was stirred with the product of Example 1H (0.215 g, 0.647 mmol) and diisopropylethylamine (0.15 mL, 0.86 mmol) in 2 mL N,N-dimethylformamide at room temperature for 1 h. After this time, the mixture was diluted with H2O. The precipitate thus formed was collected by filtration, dissolved in methanol (2 mL) and tetrahydrofuran (0.5 mL), and treated with 1N aq NaOH (0.75 mL, 0.75 mmol). The mixture was stirred at room temperature for 3 h, and precipitated with H2O. The precipitate was dissolved in ethyl acetate, and washed with water, and brine, and dried (Na2SO4) and evaporated to give the product as a tan solid (0.219 g, 0.540 mmol, 83%). 1H NMR (300 MHz, DMSO-d6) δ ppm 13.01 (br s, 1H), 8.65 (s, 1H), 8.06 (br s, 1H), 7.68 (d, 1H), 7.21 (m, 2H), 7.07 (d, 1H), 6.64 (d, 1H), 6.51 (dd, 1H), 6.35 (d, 1H), 4.92 (m, 1H), 3.71 (s, 3H), 2.22 (dd, 1H), 1.25-1.80 (m, 12H); MS (ESI+) m/z 407.2 (M+H).

Workup

  1. customThe precipitate thus formed
  2. filtrationwas collected by filtration
  3. dissolutiondissolved in methanol (2 mL)
  4. customprecipitated with H2O
  5. dissolutionThe precipitate was dissolved in ethyl acetate
  6. washwashed with water, and brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-7da80c8e792049b6aff2527037c47f3f
Source dataset
uspto-grants-2009_11
Patent number
US07622493B2

Reaction notes

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