Sodium Hydroxide → HCID 76597765, compound

HRID 1094937Notes

Reaction equation

HRID 1094937 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([CH:17]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[O:8].[C:19](N1C=CN=C1)(N1C=CN=C1)=[S:20].[N:31](=[C:33]([C:35]1[C:39]([OH:40])=[C:38]([C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=2)[N:37]([CH3:51])[N:36]=1)[CH3:34])[NH2:32].[OH-].[Na+]>C(O)C.O.CN(C)C=O>[Cl:18][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:19]([NH:32][N:31]=[C:33]([C:35]2[C:39]([OH:40])=[C:38]([C:41]3[CH:42]=[CH:43][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:45][CH:46]=3)[N:37]([CH3:51])[N:36]=2)[CH3:34])=[S:20])=[CH:17][C:6]=1[C:7]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 57421781HCID 57421781, compoundHCID 723601133-(1-hydrazonoethyl)-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-ol

Product 1

HCID 76597765HCID 76597765, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Ethyl 3-(5-amino-2-chlorobenzoylamino)propionate (122.8 mg, 0.45 mmol) was stirred with a dimethylformamide solution of thiocarbonyldiimidazole (0.1 M, 4.5 mL) at room temperature for 1 hour and with a dimethylformamide solution of 3-(1-hydrazonoethyl)-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-ol prepared in Reference Synthetic Example 14 (0.1 M, 3.0 mL) at room temperature for 6 hours. Water (3.0 mL) was added, and the precipitated solid was removed by filtration. The filtrate was separated by thin layer chromatography to give 57.0 mg of a crude product. An ethanol solution (1.0 mL) of the crude product (26.0 mg, 0.0435 mmol) was stirred with 1 M aqueous sodium hydroxide (131 μL, 0.131 mmol), and the precipitated solid was collected by filtration, washed with water and dried to give 14.6 mg of the desired product (yield 20%).

Workup

  1. customthe precipitated solid was removed by filtration
  2. customThe filtrate was separated by thin layer chromatography
  3. customto give 57.0 mg of a crude product
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-401408ea324846c0bb7ba1163565b57a
Source dataset
uspto-grants-2012_03
Patent number
US08134013B2

Reaction notes

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