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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 509934
Notes
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Reaction equation

HRID 509934 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 (27, 0.200 g, 0.32 mmol) in 15.0 mL of dichloromethane, triethylsilane (0.600 mL, 376 mmol) and trifluoroacetic acid (0.300 mL, 3.89 mmol) were added. 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, filtered, and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 25-100% ethyl acetate in hexane to give the desired compound (28, 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 concentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with 25-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-941f7bbd54704ff9b5eef6cc3448f2c0
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096593B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes