HCID 46205772, compound → HCID 16665934, compound

HRID 2366469Notes

Reaction equation

HRID 2366469 reaction equation
[C:1]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:23][CH2:22][CH2:21][N:20]4C(OC(C)(C)C)=O)=[CH:15][C:14]=3[F:31])[NH:9][C:8]=2[CH:7]=[C:6]([F:32])[CH:5]=1)(=[O:3])[NH2:2]>ClCCl.FC(F)(F)C(O)=O>[F:32][C:6]1[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:12]2[N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:23][CH2:22][CH2:21][NH:20]4)=[CH:15][C:14]=3[F:31])[NH:9][C:8]=2[CH:7]=1

Participants

4

Reactant 1

HCID 46205772HCID 46205772, compound

Product 1

HCID 16665934HCID 16665934, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 55A (360 mg) in dichloromethane (25 mL) and trifluoroacetic acid (5 mL) was stirred for 1 hour and concentrated. The concentrate was purified by HPLC (Zorbax, C-18, 250×2.54 column, Mobile phase A: 0.1% TFA in water; B: 0.1% TFA in CH3CN; 0-100% gradient). 1H NMR (CD3OD) δ 2.20-2.37 (m, 3H), 2.56-2.62 (m, 1H), 3.47-3.57 (m, 2H), 4.76 (dd, J=9.31, 7.17 Hz, 1H), 7.50-7.54 (m, 3H), 7.71 (dd, J=10.37, 2.44 Hz, 1H), 8.43 (t, J=7.93 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by HPLC (Zorbax, C-18, 250×2.54 column, Mobile phase A: 0.1% TFA in water; B: 0.1% TFA in CH3CN; 0-100% gradient)

Sources & evidence

ORD record
ord-76c0a0a0285340499247d90903915ce8
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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