Ethylamine → HCID 1266366, compound

HRID 1988681Notes

Reaction equation

HRID 1988681 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)[N:4]=1.C(N1C=CN=C1)([N:25]1[CH:29]=[CH:28]N=C1)=O.C(N)C>ClCCl.O1CCCC1>[CH2:29]([NH:25][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:12]([N:5]2[C:6]3[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=3[C:3]([C:2]([F:1])([F:22])[F:21])=[N:4]2)=[CH:13][CH:14]=1)[CH3:28]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 682631,1'-CarbonyldiimidazoleHCID 8918604-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]benzoic acid

Product 1

HCID 1266366HCID 1266366, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]benzoic acid (310 mg, 1.0 mmol) in dichloromethane (5 ml) was treated with 1,1′-carbonyldiimidazole (162 mg, 1.0 mmol) at room temperature under argon. This mix was stirred for 30 minutes and then treated with a 2M solution of ethylamine in tetrahydrofuran (0.5 ml). The whole mix was stirred at room temperature for 2 hours. The reaction mixture was washed with saturated aqueous sodium bicarbonate. The organic layer was separated, dried over sodium sulphate and reduced to minimum volume by rotary evaporation to give a beige solid (250 mg) which was purified by column chromatography on a 5 g pre-packed silica column, eluting from 0-50% ethyl acetate in petroleum ether to give the title compound as a colourless solid (128 mg, 38%).

Workup

  1. additionThe whole mix
  2. stirringwas stirred at room temperature for 2 hours
  3. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. customreduced to minimum volume by rotary evaporation

Sources & evidence

ORD record
ord-c416b1ebc92a4e0b8d485c4a40c96e5b
Source dataset
uspto-grants-2010_01
Patent number
US07642256B2

Reaction notes

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