Diisopropylethylamine → HCID 56932773, compound

HRID 1972575Notes

Reaction equation

HRID 1972575 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:14][C@@H:13]2[CH2:26][NH:27][CH:28]([CH3:30])[CH3:29])=[CH:8][CH:7]=1)([OH:5])[CH3:4].[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([S:39](Cl)(=[O:41])=[O:40])[CH:34]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:30][CH:28]([N:27]([CH2:26][C@H:13]1[CH2:14][N:15]([S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])[CH2:16][CH2:17][N:12]1[C:9]1[CH:8]=[CH:7][C:6]([C:3]([OH:5])([CH3:4])[C:2]([F:1])([F:31])[F:32])=[CH:11][CH:10]=1)[S:39]([C:35]1[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=1)(=[O:41])=[O:40])[CH3:29]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 66582708HCID 66582708, compound

Product 1

HCID 56932773HCID 56932773, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1,1-trifluoro-2-(4-((2S)-2-(((1-methylethyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (0.100 g, 0.203 mmol, Example 195, Step 1) in CH2Cl2 (5.0 mL) was added 4-dimethylaminopyridine (0.005 g, 0.061 mmol), pyridine-3-sulfonyl chloride (0.072 g, 0.407 mmol, WAKO, Richmond, Va.) and Hünig's base (0.106 mL, 0.610 mmol). After 2 h at room temperature, the solvent was removed and the crude product was purified by column chromatography (40 g of silica, 20 to 40% acetone in hexanes) to give N-(1-methylethyl)-N-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyridinesulfonamide (0.120 g) as a mixture of two isomers.

Workup

  1. customthe solvent was removed
  2. customthe crude product was purified by column chromatography (40 g of silica, 20 to 40% acetone in hexanes)

Sources & evidence

ORD record
ord-cd0e31afff334c4691ad4e4d16b28b13
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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