Trifluoroacetic acid → HCID 57537673, compound

HRID 1693737Notes

Reaction equation

HRID 1693737 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:14]([C:16]3[O:17][CH:18]=[CH:19][N:20]=3)[OH:15])[CH:11]=[CH:12][CH:13]=2)=[CH:6][N:5]=[C:4]2[N:21](COCC[Si](C)(C)C)[CH:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:3]=12.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:14]([C:16]3[O:17][CH:18]=[CH:19][N:20]=3)[OH:15])[CH:11]=[CH:12][CH:13]=2)=[CH:6][N:5]=[C:4]2[NH:21][CH:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:3]=12

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57537679HCID 57537679, compound

Product 1

HCID 57537673HCID 57537673, compoundYield 16.1%

Procedure

{3-[4-Chloro-3-(2-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-oxazol-2-yl-methanol (0.040 mmol) was treated with 1 mL neat TFA. After 1 h, the TFA was removed in vacuo. The residue was treated with ethylene diamine (0.5 mL) and THF (1 mL) for 20 min. The mixture was concentrated and purified by preparative LCMS to afford {3-[4-chloro-3-(2-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-oxazol-2-yl-methanol (2.7 mg, 16%) MS: m/z 420 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 5.88 (d, 1H), 6.48 (d, 1H), 7.15 (d, 1H), 7.23 (m, 2H), 7.38-7.46 (m, 5H), 7.52 (br s, 1H), 7.71 (s, 1H), 8.04 (s, 1H), 8.19 (s, 1H).

Workup

  1. customthe TFA was removed in vacuo
  2. additionThe residue was treated with ethylene diamine (0.5 mL) and THF (1 mL) for 20 min
  3. concentrationThe mixture was concentrated
  4. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-4cf08cd05eb7446397203cfc8f2b87e4
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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