Triethylamine → HCID 86670366, compound

HRID 1972494Notes

Reaction equation

HRID 1972494 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:37])([F:36])[C:10]([C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][C@@H:23]2[CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2[CH3:35])=[CH:18][CH:17]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].C(N(CC)CC)C.[Cl:45][C:46]1[N:51]=[CH:50][C:49]([S:52](Cl)(=[O:54])=[O:53])=[CH:48][CH:47]=1>C(Cl)Cl>[Cl:45][C:46]1[N:51]=[CH:50][C:49]([S:52]([N:25]2[CH2:26][CH2:27][N:22]([C:19]3[CH:20]=[CH:21][C:16]([C:10]([OH:15])([C:9]([F:8])([F:36])[F:37])[C:11]([F:14])([F:13])[F:12])=[CH:17][CH:18]=3)[C@@H:23]([CH2:28][N:29]3[CH2:34][CH2:33][O:32][CH2:31][C@H:30]3[CH3:35])[CH2:24]2)(=[O:54])=[O:53])=[CH:48][CH:47]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 86670367HCID 86670367, compound

Product 1

HCID 86670366HCID 86670366, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The 1,1,1,3,3,3-hexafluoro-2-(4-((2R)-2-(((3S)-3-methyl-4-morpholinyl)methyl)-1-piperazinyl)phenyl)-2-propanol trifluoroacetate (115 mg, 0.172 mmol) was dissolved in CH2Cl2 (30 mL) and was chilled to 0° C. To this solution was triethylamine (96 μl, 0.687 mmol) followed by 6-chloropyridine-3-sulfonyl chloride (40.1 mg, 0.189 mmol, Organic Process Research & Development 2009, 13, 875). The mixture was warmed slowly to room temp and stirred for 2 h. Afterwards, the mixture was concentrated to give 2-(4-((S)-4-((6-chloropyridin-3-yl)sulfonyl)-2-(((R)-3-methylmorpholino)methyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol.

Workup

  1. temperatureThe mixture was warmed slowly to room temp
  2. concentrationAfterwards, the mixture was concentrated

Sources & evidence

ORD record
ord-aa916b2931234ae7aa0ff316e7725212
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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