Trifluoroacetic acid → HCID 16665853, compound

HRID 2366466Notes

Reaction equation

HRID 2366466 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]=[CH:6][CH:5]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>ClCCl>[F:31][C:14]1[CH:15]=[C:16]([CH:19]2[CH2:23][CH2:22][CH2:21][NH:20]2)[CH:17]=[CH:18][C:13]=1[C:10]1[NH:9][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46206100HCID 46206100, compound

Product 1

HCID 16665853HCID 16665853, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 50E (1.5 g) in dichloromethane (50 mL) was treated with TFA (10 mL), 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 2.21-2.36 (m, 3H), 2.54-2.63 (m, 1H), 3.47-3.59 (m, 2H), 4.76 (dd, J=9.51, 7.06 Hz, 1H), 7.43 (t, J=7.83 Hz, 1H), 7.50-7.55 (m, 2H), 7.84 (d, J=7.36 Hz, 1H), 7.98 (d, J=7.67 Hz, 1H), 8.42 (t, J=8.13 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-18afeeab609445a7b6441815a9f4c5b6
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

Loading…