Triethylamine → HCID 178419181, compound

HRID 1946537Notes

Reaction equation

HRID 1946537 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18][CH2:19][OH:20])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:21]([CH3:23])[CH3:22])=[CH:4][CH:3]=1.[BH3:24].C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH3:32][S:33]([O:20][CH2:19][CH2:18][CH:14]1[C:13]2[N:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:10]([CH:21]([CH3:23])[CH3:22])=[N:11][C:12]=2[CH2:17][CH2:16][CH2:15]1)(=[O:35])=[O:34].[BH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178419180HCID 178419180, compound

Product 1

HCID 178419181HCID 178419181, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred suspension of Intermediate 76 (830 mg) in Dichloromethane (DCM) (40 mL), under nitrogen, was treated with triethylamine (0.501 mL) then cooled to ca. 0° C. (ice bath). Methanesulfonyl chloride (0.222 mL) was added via syringe, then the cooling bath was removed and stirring continued for 2 h. The solution was partitioned between aqueous ammonium chloride (200 ml) and DCM (200 ml). The layers were separated and the aqueous phase was further extracted with DCM (200 ml). The combined organic extracts were washed with water (200 mL), dried (Na2SO4), filtered through a hydrophobic frit and evaporated in vacuo. The crude product was purified by column chromatography (silica, 0-25% Methanol in DCM). The appropriate fractions were combined and concentrated to afford the title compound, 368 mg. LC/MS (M-BH2)-411/413, Rt 2.18 mins (5 min run, TFA modifier).

Workup

  1. customthe cooling bath was removed
  2. customThe solution was partitioned between aqueous ammonium chloride (200 ml) and DCM (200 ml)
  3. customThe layers were separated
  4. extractionthe aqueous phase was further extracted with DCM (200 ml)
  5. washThe combined organic extracts were washed with water (200 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered through a hydrophobic frit
  8. customevaporated in vacuo
  9. customThe crude product was purified by column chromatography (silica, 0-25% Methanol in DCM)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d7523f9e60944d068bfe0137fa16d97d
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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