Trifluoroacetic acid → HCID 86670408, compound

HRID 1972618Notes

Reaction equation

HRID 1972618 reaction equation
[CH3:1][S:2]([N:5]([CH2:12][C@@H:13]1[N:18]([C:19]2[N:24]=[CH:23][C:22]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][N:20]=2)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O.C(N(CC)CC)C.[N+:56]([C:59]1[S:63][C:62]([S:64](Cl)(=[O:66])=[O:65])=[CH:61][CH:60]=1)([O-:58])=[O:57]>C(Cl)Cl>[N+:56]([C:59]1[S:63][C:62]([S:64]([N:15]2[CH2:16][CH2:17][N:18]([C:19]3[N:24]=[CH:23][C:22]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:28])([F:29])[F:27])=[CH:21][N:20]=3)[C@@H:13]([CH2:12][N:5]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:2]([CH3:1])(=[O:3])=[O:4])[CH2:14]2)(=[O:66])=[O:65])=[CH:61][CH:60]=1)([O-:58])=[O:57]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 217873475-Nitrothiophene-2-sulfonyl chlorideHCID 86670407HCID 86670407, compound

Product 1

HCID 86670408HCID 86670408, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 5-mL vial was charged with tert-butyl (3R)-3-(((methylsulfonyl)(phenyl)amino)methyl)-4-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-1-piperazinecarboxylate (0.229 g, 0.373 mmol), TFA (1.0 mL, 13 mmol) and CH2Cl2 (2 mL). The mixture was stirred at room temperature for 35 min and then concentrated. CH2Cl2 (1 mL) was added to the residue followed by triethylamine (0.60 mL, 4.3 mmol). The mixture was stirred at room temperature for 10 min and then a solution of 5-nitrothiophene-2-sulfonyl chloride (0.104 g, 0.456 mmol, Enamine LLC, Monmouth Jct. NJ) in CH2Cl2 (1 mL) was added drop wise. After stirring at room temperature for 40 min, the mixture was concentrated and purified by column chromatography (50 g of silica gel, 0 to 60% EtOAc in hexanes) to afford N-(((2R)-4-((5-nitro-2-thiophenyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-N-phenylmethanesulfonamide (0.131 g) as a light-brown foam.

Workup

  1. concentrationconcentrated
  2. additionCH2Cl2 (1 mL) was added to the residue
  3. stirringThe mixture was stirred at room temperature for 10 min
  4. stirringAfter stirring at room temperature for 40 min
  5. concentrationthe mixture was concentrated
  6. custompurified by column chromatography (50 g of silica gel, 0 to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-92338a6584cd414b874d71c11d4d0f1b
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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