Water → HCID 86743042, compound

HRID 1762272Notes

Reaction equation

HRID 1762272 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:5]([C:13]2[C:14]([F:23])=[CH:15][C:16]3[S:20][C:19](=O)[NH:18][C:17]=3[CH:22]=2)[N:6]=[C:7]2[C:12]=1[CH2:11][CH2:10][CH2:9][CH2:8]2.[CH2:24](Br)[C:25]#[CH:26].[OH2:28]>CN(C)C=O>[Cl:3][C:4]1[N:5]([C:13]2[C:14]([F:23])=[CH:15][C:16]3[S:20](=[O:28])[CH2:19][N:18]([CH2:24][C:25]#[CH:26])[C:17]=3[CH:22]=2)[N:6]=[C:7]2[C:12]=1[CH2:11][CH2:10][CH2:9][CH2:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 14053647HCID 14053647, compound

Product 1

HCID 86743042HCID 86743042, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (60% oil; 50 mg) in N,N-dimethylformamide (3 ml) was cooled to 0° C., and 3-chloro-2-(6-fluoro-2(3H)-benzothiazolon-5-yl)-4,5,6,7-tetrahydro-2H-indazole (390 mg) was added thereto at 0°, followed by stirring at the same temperature for 30 minutes. To the suspension, propargyl bromide (160 mg) was added, and the resultant mixture was heated to a temperature of 50° to 60° C. and allowed to react at the same temperature for 2 to 3 hours. Water was added to the reaction mixture, which was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel thin layer chromatography using a mixture of ethyl acetate and hexane (1:4) as a developing solvent to give 3-chloro-2-[6-fluoro-3-(2-propynyl)-2H-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-indazole (24.1 gg). m.p., 130°-132° C.

Workup

  1. customat 0°
  2. customto react at the same temperature for 2 to 3 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel thin layer chromatography
  8. additiona mixture of ethyl acetate and hexane (1:4) as a developing solvent

Sources & evidence

ORD record
ord-cae55f6b48c3442ebd97c3bf8c8b0db3
Source dataset
uspto-grants-1989_05
Patent number
US04831150

Reaction notes

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