Trifluoroacetic acid → HCID 10110755, compound

HRID 917314Notes

Reaction equation

HRID 917314 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:40])[CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH: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]([CH:19]3[CH2:18][CH2:17][CH:16]([O:15][CH2:14][C:13]([OH:40])=[O:12])[CH2:21][CH2:20]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 69397730HCID 69397730, compound

Product 1

HCID 10110755HCID 10110755, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (TFA) (2 ml) is added to a solution of {4-[8-(3-cyano-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexyloxy}-acetic acid tert-butyl ester (182 mg, 0.41 mmol) in CH2Cl2 (2 ml) at 0° C. The solution is stirred at room temperature for 1 hour, concentrated, and azeotroped with toluene (×3). Purification by chromatography on silica gel, eluting with 7% methanol in CH2Cl2 gives the product. MS (ES+) [M+H]+ 388.04

Workup

  1. concentrationconcentrated
  2. customazeotroped with toluene (×3)
  3. customPurification by chromatography on silica gel
  4. washeluting with 7% methanol in CH2Cl2
  5. customgives the product

Sources & evidence

ORD record
ord-59b370acac8b4094be2b9baa03393ee8
Source dataset
uspto-grants-2007_09
Patent number
US07273875B2

Reaction notes

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