Triethylamine → HCID 178493632, compound

HRID 1944747Notes

Reaction equation

HRID 1944747 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][C@@H:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(CC)CC.[OH:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][C:30]=1[O:39][CH3:40]>C(Cl)Cl>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:12]([NH:11][C:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([NH:2][S:35]([C:32]3[CH:33]=[CH:34][C:29]([OH:28])=[C:30]([O:39][CH3:40])[CH:31]=3)(=[O:37])=[O:36])[CH2:4][CH2:5]2)=[O:10])[CH3:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20235349HCID 20235349, compoundHCID 178462116HCID 178462116, compound2×

Product 1

HCID 178493632HCID 178493632, compoundYield 4.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-4-Amino-N—((R)-1-(4-fluorophenyl)ethyl)cyclohexanecarboxamide hydrochloride (Intermediate 45, 200 mg, 0.66 mmol) and Et3N (371 ul, 2.66 mmol) were dissolved in DCM (10 ml). 4-Hydroxy-3-methoxy-benzenesulphonyl chloride (178 mg, 0.798 mmol) was added, and the reaction mixture was stirred for 3 hr at room temperature, after which LCMS indicated that the reaction was complete. The mixture was concentrated in vacuo, and the crude material was purified via reverse phase chromatography on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA). Fractions containing the product were lyophilized to yield the title compound as a white solid (14 mg, 0.031 mmol). MS MH+ 451.1

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe crude material was purified via reverse phase chromatography on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA)
  3. additionFractions containing the product

Sources & evidence

ORD record
ord-d0078a54174740ef830544f35dfda6e2
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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