1,2-Dichloroethane → HCID 58011813, compound

HRID 660940Notes

Reaction equation

HRID 660940 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:10](=[O:20])[N:9]([CH2:21][C:22]([OH:24])=O)[N:8]=2)=[CH:4][CH:3]=1.[F:25][C:26]([F:38])([F:37])[C:27]1[CH:28]=[C:29]([C:33]([NH2:36])([CH3:35])[CH3:34])[CH:30]=[CH:31][CH:32]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:10](=[O:20])[N:9]([CH2:21][C:22]([NH:36][C:33]([CH3:35])([C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([C:26]([F:25])([F:37])[F:38])[CH:28]=3)[CH3:34])=[O:24])[N:8]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 194252732-[3-(Trifluoromethyl)phenyl]propan-2-amineHCID 58011885HCID 58011885, compound

Product 1

HCID 58011813HCID 58011813, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The carboxylic acid from Example 154A (150 mg, 0.41 mmol) and 1-methyl-1-(3-trifluoromethyl-phenyl)ethylamine (Example 1A, 91.2 mg, 0.45 mmol) are placed in 4 ml DMF and treated at RT with 66.1 mg (0.49 mmol) of HOBt. After 10 mins, 101.6 mg (0.53 mmol) of EDC are added and the mixture stirred overnight at RT. It is then treated with water and ethyl acetate. The phases are separated, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water, then with sat. sodium chloride solution, dried by filtration through an Extrelut cartridge and freed of the volatile components on the rotary evaporator. The residue is purified by chromatography on silica gel (Biotage cartridge 25M, eluent: cyclohexane/ethyl acetate 1:1). 192 mg (85% of theory) of the title compound are thus obtained.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. dry with materialwith sat. sodium chloride solution, dried by filtration through an Extrelut cartridge
  5. customfreed of the volatile components on the rotary evaporator
  6. customThe residue is purified by chromatography on silica gel (Biotage cartridge 25M, eluent: cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-466cd7eb923a4ec0aab95bd63db61485
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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