Triethylamine → HCID 71581865, compound

HRID 2174925Notes

Reaction equation

HRID 2174925 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:17]=[CH:16][C:15]2[C:11](=[CH:12][N:13]([CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:14]=2)[C:10]=1[CH3:25])=[O:8].C(N(CC)CC)C.[F:33][C:34]([S:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)([F:36])[F:35]>C(Cl)Cl>[CH3:2][O:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:17]=[CH:16][C:15]2[C:11](=[CH:12][N:13]([CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([C:42](=[O:43])[C:41]4[CH:45]=[CH:46][C:38]([S:37][C:34]([F:36])([F:33])[F:35])=[CH:39][CH:40]=4)[CH2:23][CH2:24]3)[N:14]=2)[C:10]=1[CH3:25])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27778654-(Trifluoromethylthio)benzoyl chlorideHCID 89601954HCID 89601954, compound

Product 1

HCID 71581865HCID 71581865, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

60 mg of the amine prepared in Example 1a were first dissolved in 2 ml DCM at 0° C. 0.034 ml of triethylamine and 43.2 mg of 4-[(trifluoromethyl)sulphanyl]benzoyl chloride were then added and the mixture stirred for 2 hrs at 0° C. The reaction mixture was then diluted with DCM and washed with 1-molar hydrochloric acid, saturated sodium hydrogen carbonate solution (pH 9) and saturated sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4. Gradient: DCM/Methanol 0-10%. The product fraction was taken up in ethyl acetate and extracted twice with saturated sodium hydrogen carbonate solution. The organic phase was concentrated and the residue again purified by HPLC. Yield: 26.5 mg of the title compound.

Workup

  1. washwashed with 1-molar hydrochloric acid, saturated sodium hydrogen carbonate solution (pH 9) and saturated sodium chloride solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified chromatographically on the Biotage SP4
  6. extractionextracted twice with saturated sodium hydrogen carbonate solution
  7. concentrationThe organic phase was concentrated
  8. customthe residue again purified by HPLC

Sources & evidence

ORD record
ord-bd3a48491f84484ba5c60e0b201b9ff5
Source dataset
uspto-grants-2015_06
Patent number
US09062041B2

Reaction notes

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