Triethylamine → HCID 86670420, compound

HRID 1972639Notes

Reaction equation

HRID 1972639 reaction equation
[F:1][C:2]([F:22])([F:21])[C@:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]2[C:18]#[C:19][CH3:20])=[CH:8][CH:7]=1)([OH:5])[CH3:4].C(N(CC)CC)C.[Cl:30][C:31]1[N:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[Cl:30][C:31]1[N:36]=[CH:35][C:34]([S:37]([N:15]2[CH2:16][CH2:17][N:12]([C:9]3[CH:8]=[CH:7][C:6]([C@@:3]([OH:5])([CH3:4])[C:2]([F:1])([F:21])[F:22])=[CH:11][CH:10]=3)[CH:13]([C:18]#[C:19][CH3:20])[CH2:14]2)(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 66582986HCID 66582986, compound

Product 1

HCID 86670420HCID 86670420, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2S)-1,1,1-trifluoro-2-(4-(2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-2-propanol (0.190 g, 0.608 mmol) in DCM (5.0 mL) was added triethylamine (0.254 mL, 1.83 mmol, Aldrich, St. Louis, Mo.). The reaction mixture was cooled to 0° C. and 6-chloropyridine-3-sulfonyl chloride (0.155 g, 0.730 mmol, Organic Process Research & Development 2009, 13, 875) was added in one portion. After the addition, the resulting mixture was stirred at 0° C. for 15 min. The reaction mixture was concentrated and the crude product was purified by column chromatography (40 g of silica, 10 to 30% acetone in hexanes) to afford (2S)-2-(4-(4-((6-chloro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (0.240 g) as a white foam.

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude product was purified by column chromatography (40 g of silica, 10 to 30% acetone in hexanes)

Sources & evidence

ORD record
ord-207235d1fff14fcdb2e436d2e5311a07
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

Loading…