HCID 136506542, compound → HCID 135948891, compound

HRID 1034962Notes

Reaction equation

HRID 1034962 reaction equation
C(OC(=O)[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:30]3[C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[C:23](=[O:31])[NH:22][C:21]=3[N:20]([CH3:32])[N:19]=2)=[CH:14][CH:13]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:30]3[C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[C:23](=[O:31])[NH:22][C:21]=3[N:20]([CH3:32])[N:19]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 136506542HCID 136506542, compound

Product 1

HCID 135948891HCID 135948891, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Example 39 (90 mg, 0.2 mmol) in trifluoroacetic acid (10 mL) was stirred at 50° C. for 4 hours. After cooling, the mixture was concentrated and the residue purified by HPLC (Zorbax, C-18, 250×2.54 column, Mobile phase A 0.1% trifluoroacetic acid in water, B 0.1% trifluoroacetic acid in acetonitrile, 0-100% gradient) to provide 70 mg of the title compound as the trifluoroacetate salt. 1H NMR (CD3OD) □ 1.53-1.63 (m, 2H), 1.71-1.80 (m, 2H), 2.42-2.54 (m, 4H), 3.92 (s, 3H), 4.21 (s, 2H), 7.52-7.65 (m, 4H).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. customthe residue purified by HPLC (Zorbax, C-18, 250×2.54 column, Mobile phase A 0.1% trifluoroacetic acid in water, B 0.1% trifluoroacetic acid in acetonitrile, 0-100% gradient)

Sources & evidence

ORD record
ord-5fa94916dac84a3c99788a48b1b89713
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

Loading…