Trifluoroacetic acid → HCID 59437449, compound

HRID 2382907Notes

Reaction equation

HRID 2382907 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([N:23]=[C:24]([NH:26][C:27](=[O:41])[C:28]4[CH:33]=[CH:32][C:31]([CH2:34][N:35]5[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]5)=[CH:30][CH:29]=4)[N:25]=3)[CH:22]=2)[CH:6]=[CH:7][C:8]=1[O:9]CC1C=CC=CC=1.FC(F)(F)C(O)=O>>[OH:9][C:8]1[CH:7]=[CH:6][C:5]([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([N:23]=[C:24]([NH:26][C:27](=[O:41])[C:28]4[CH:29]=[CH:30][C:31]([CH2:34][N:35]5[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]5)=[CH:32][CH:33]=4)[N:25]=3)[CH:22]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59437565HCID 59437565, compound

Product 1

HCID 59437449HCID 59437449, compoundYield 11.3%

Conditions

Temperature
75 °C

Procedure

N-(6-{3-(methyloxy)-4-[(phenylmethyl)oxy]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-yl)-4-(piperidin-1-ylmethyl)benzamide (14.9 mg, 0.027 mmol) was treated with trifluoroacetic acid (2 mL) and the reaction mixture was stirred for 1 hour at 75° C. The reaction mixture was cooled and the solvent removed in vacuo. The residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a white solid (1.4 mg, 11%). HPLC, Rt: 2.23 min (purity: 99%). LC/MS M+(ESI): 458.2, M−(ESI) 456.2.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue dissolved in DMSO (1.5 mL)
  4. custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-a92790893bb246d1ba4893cecaaa3c48
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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