Trifluoroacetic acid → HCID 57619310, compound

HRID 1256843Notes

Reaction equation

HRID 1256843 reaction equation
C(OC(=O)[N:7]([C:16]1[S:17][C:18]([CH2:21][C:22]2[C:30]3[C:25](=[N:26][CH:27]=[C:28]([Cl:31])[CH:29]=3)[NH:24][CH:23]=2)=[CH:19][N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:31][C:28]1[CH:29]=[C:30]2[C:22]([CH2:21][C:18]3[S:17][C:16]([NH:7][CH2:8][C:9]4[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=4)=[N:20][CH:19]=3)=[CH:23][NH:24][C:25]2=[N:26][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57619315HCID 57619315, compound

Product 1

HCID 57619310HCID 57619310, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of crude [5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-thiazol-2-yl]-(4-fluoro-benzyl)-carbamic acid tert-butyl ester (628, 0.186 mmol theory) in dichloromethane (5 mL) at room temperature was added trifluoroacetic acid (1 mL) and the reaction was allowed to stir overnight. The solvent was removed in vacuo and the residue taken up in ethyl acetate and then washed with saturated aqueous potassium carbonate making sure basicity was reached. The layers were separated and the aqueous layer was back-extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated in vacuo to give the crude product which was purified by silica gel chromatography (0-10% methanol/ethyl acetate). The solvent was removed in vacuo and the material was triturated with dichloromethane to give the desired compound as an off-white solid (20 mg, 29% over 2 steps) consistent with compound structure by 1H-NMR and MS (ESI): [M+H+]+=372.9.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with saturated aqueous potassium carbonate making sure basicity
  3. customThe layers were separated
  4. extractionthe aqueous layer was back-extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. customevaporated in vacuo
  7. customto give the crude product which
  8. customwas purified by silica gel chromatography (0-10% methanol/ethyl acetate)
  9. customThe solvent was removed in vacuo
  10. customthe material was triturated with dichloromethane

Sources & evidence

ORD record
ord-69a126b2c4634a7ca3c2ecf0d9ccc775
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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