Trifluoroacetic acid → Carbamic acid, N-[4-chloro-5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-2-thiazolyl]-, 1,1-dimethylethyl ester

HRID 1952138Notes

Reaction equation

HRID 1952138 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1[S:9][C:10]([CH:14]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[N:18]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:17]=2)O)=[C:11]([Cl:13])[N:12]=1)([CH3:4])([CH3:3])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1[S:9][C:10]([CH2:14][C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[N:18]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:27])=[O:28])[CH:17]=2)=[C:11]([Cl:13])[N:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57619425Carbamic acid, N-[4-chloro-5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]hydroxymethyl]-2-thiazolyl]-, 1,1-dimethylethyl ester

Product 1

HCID 57619385Carbamic acid, N-[4-chloro-5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-2-thiazolyl]-, 1,1-dimethylethyl esterYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-[(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-4-chloro-thiazol-2-yl-carbamic acid tert-butyl ester (590, 0.200 g, 0.32 mmol) in dichloromethane (15.0 mL) were added triethylsilane (0.600 mL, 376 mmol) and trifluoroacetic acid (0.300 mL, 3.89 mmol). The reaction was stirred at room temperature for 3 hours, then concentrated, poured into aqueous potassium carbonate, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 25% to 100% ethyl acetate in hexane to give the desired compound (591, 0.155 g, 88.7%). MS (ESI) [M+H+]+=538.9.

Workup

  1. concentrationconcentrated
  2. additionpoured into aqueous potassium carbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 25% to 100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fd0550d61fe3441285a2830dda442472
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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