Trifluoroacetic acid → HCID 86587611, compound

HRID 1594060Notes

Reaction equation

HRID 1594060 reaction equation
C(OC(=O)C[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[N:14]=1)(C)(C)C.F[C:22](F)(F)[C:23]([OH:25])=[O:24]>ClCCl>[F:19][C:15]1([CH2:22][C:23]([OH:25])=[O:24])[CH:16]=[CH:17][CH:18]=[C:13]([C:9]2[NH:8][CH:12]=[CH:11][N:10]=2)[NH:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68495227[2-(6-Fluoropyridin-2-yl)-imidazol-1-yl]acetic acid tert-butyl ester

Product 1

HCID 86587611HCID 86587611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(6-fluoropyridin-2-yl)-imidazol-1-yl]acetic acid tert-butyl ester (630 mg; 2.27 mmol) and trifluoroacetic acid (4 mL) in dichloromethane (4 mL) is stirred at room temperature for 5 hr. The reaction mixture is concentrated. The residue is treated with 3M HCl in ethyl acetate (10 mL) and the suspension stirred at room temperature for 1 hr. The precipitate is collected, washed with ethyl acetate, and dried to give 2-Fluoro-6-(1H-imidazol-2-yl)-pyridine acetic acid as a tan solid (581 mg), 1H NMR (d6DMSO) δ 8.35-8.26 (m, 2H), 7.83 (s, 1H), 7.76 (s, 1H), 7.44-7.41(m. 1H), 5.40 (s, 2H). LCMS: 222.1 (MH+).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionThe residue is treated with 3M HCl in ethyl acetate (10 mL)
  3. customThe precipitate is collected
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-ea9b04f08fb64bd2a8a52988974c3429
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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