Trifluoroacetic acid → HCID 10023153, compound

HRID 2376631Notes

Reaction equation

HRID 2376631 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13](=[O:40])[CH2:14][O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[C:24]3[C:29](=[C:30]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[N:39])[CH:33]=4)[N:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)[CH2:18][CH2:17]1)(C)(C)C>C(Cl)Cl>[C:38]([C:34]1[CH:33]=[C:32]([C:30]2[N:31]=[C:22]([N:19]3[CH2:20][CH2:21][CH:16]([O:15][CH2:14][C:13]([OH:40])=[O:12])[CH2:17][CH2:18]3)[CH:23]=[C:24]3[C:29]=2[N:28]=[CH:27][CH:26]=[CH:25]3)[CH:37]=[CH:36][CH:35]=1)#[N:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69206959HCID 69206959, compound

Product 1

HCID 10023153HCID 10023153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

TFA (1 ml) is added to a solution of {1-[8-(3-cyano-phenyl)-[1,7]naphthyridin-6-yl]-piperidin-4-yloxy}-acetic acid tert-butyl ester (200 mg, 0.45 mmol) in CH2Cl2 (2 ml) at 0° C. The reaction mixture is stirred at 0° C. for 10 minutes then at room temperature for 1.5 hours and is then concentrated. The residue is partitioned between ethyl acetate and water and the aqueous layer is adjusted to pH 5 with 1M KOH. The aqueous layer is extracted with ethyl acetate (×3) and the combined ethyl acetate extracts are dried (MgSO4), filtered and concentrated. Purification by chromatography on silica gel, eluting with 1% MeOH in CH2Cl2 gives the product. MS (ES+) Observed [M+H]+3 89.05

Workup

  1. waitat room temperature for 1.5 hours
  2. concentrationis then concentrated
  3. customThe residue is partitioned between ethyl acetate and water
  4. extractionThe aqueous layer is extracted with ethyl acetate (×3)
  5. dry with materialthe combined ethyl acetate extracts are dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography on silica gel
  9. washeluting with 1% MeOH in CH2Cl2
  10. customgives the product

Sources & evidence

ORD record
ord-ccac5a3d09534436a2dacf2845c16dec
Source dataset
uspto-grants-2008_12
Patent number
US07468370B2

Reaction notes

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