Trifluoroacetic acid → HCID 16665847, compound

HRID 2366456Notes

Reaction equation

HRID 2366456 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][CH:14]=3)[NH:9][C:8]=2[CH:7]=[C:6]([Cl:31])[CH:5]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>ClCCl>[Cl:31][C:6]1[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:12]2[N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([CH:19]4[CH2:23][CH2:22][CH2:21][NH:20]4)=[CH:17][CH:18]=3)[NH:9][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46205770HCID 46205770, compound

Product 1

HCID 16665847HCID 16665847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 44C (410 mg) in dichloromethane (20 mL) was treated with TFA (4 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 (DMSO-d6) δ 2.04-2.20 (m, 3H), 2.41-2.52 (m, 2H), 3.33-3.46 (m, 2H), 4.65-4.71 (m, 1H), 7.72 (d, J=8.29 Hz, 2H), 7.81-7.84 (m, 1H), 7.95 (s, 1H), 8.34 (d, J=8.29 Hz, 2H), 8.94 (s, 1H), 9.14 (s, 1H), 9.73 (s, 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-42334105d7e049ef9545988ea5ff7e2f
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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