HCID 136660218, compound → HCID 136414506, compound

HRID 1034967Notes

Reaction equation

HRID 1034967 reaction equation
COC1C=CC(C[N:8]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[C:38]4[C:37]5[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=5[C:31](=[O:39])[NH:30][C:29]=4[N:28]([CH3:40])[N:27]=3)[CH:21]=2)C(=O)OCC2C=CC=CC=2)=CC=1>FC(F)(F)C(O)=O>[NH2:8][CH2:19][C:20]1[CH:21]=[C:22]([C:26]2[C:38]3[C:37]4[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=4[C:31](=[O:39])[NH:30][C:29]=3[N:28]([CH3:40])[N:27]=2)[CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 1

HCID 136660218HCID 136660218, compound

Product 1

HCID 136414506HCID 136414506, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 56F (3.4 g) in trifluoroacetic acid (20 mL) was stirred at 55° C. for 6 hours. 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 give the title compound (1.3 g, 50%) as the trifluoroacetate salt. 1H NMR (CD3OD) □ 2.28-2.40 (m, 2H), 2.44-2.57 (m, 2H), 3.08-3.37 (m, 4H), 4.69 (s, 3H), 4.93 (s, 2H), 8.26-8.37 (m, 3H), 8.43 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. 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-e112554b523b46ba80728416d5f7f1c5
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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