Sodium hydride → HCID 57762817, compound

HRID 230686Notes

Reaction equation

HRID 230686 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([CH2:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)[N:4]=1.C(N(C(C)C)CC)(C)C.Cl[CH2:32][CH2:33][CH2:34][C:35](Cl)=[O:36].[H-].[Na+]>ClCCl>[F:21][C:2]([F:1])([F:20])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([N:17]3[CH2:32][CH2:33][CH2:34][C:35]3=[O:36])=[CH:18][CH:19]=2)[N:4]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 783704-Chlorobutyryl chlorideHCID 81531DiisopropylethylamineHCID 57762786HCID 57762786, compound

Product 1

HCID 57762817HCID 57762817, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-{[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]methyl}aniline (166 mg, 0.56 mmol) in dichloromethane (4 ml) was treated with diisopropylethylamine (1.12 mmol, 146 mg) followed by 4-chlorobutyryl chloride (80 mg, 0.56 mmol). After stirring at room temperature for 15 minutes a solid suspension of sodium hydride (60% in mineral oil) (22 mg, 0.55 mmol) was added and stirring continued for 30 minutes. The dichloromethane was removed by blowing with air and dimethylformamide added (3 ml) and stirring continued for 30 minutes. The reaction mix was partitioned between dichloromethane and water (2×5 ml). The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give a yellow oil (190 mg) which was purified by mass directed auto prep to give the title compound as a yellow oil (39 mg, 19%).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitcontinued for 30 minutes
  4. customThe dichloromethane was removed
  5. additionadded (3 ml)
  6. stirringstirring
  7. waitcontinued for 30 minutes
  8. additionThe reaction mix
  9. customwas partitioned between dichloromethane and water (2×5 ml)
  10. dry with materialThe organic layer was dried over sodium sulphate
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-91b96d343fef4665a8982434c5bd653a
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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