Trifluoroacetic acid → HCID 90412514, compound

HRID 1521969Notes

Reaction equation

HRID 1521969 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][C:16]([CH:18]4[CH2:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]4)=[CH:17][C:10]=23)=[C:5]([O:31][CH3:32])[CH:4]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[CH3:32][O:31][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][C:16]([CH:18]3[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]3)=[CH:17][C:10]=12)[C:1]#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90412400HCID 90412400, compound

Product 1

HCID 90412514HCID 90412514, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 137A (75 mg, 0.17 mmol) in dichloromethane (3 mL) was treated with trifluoroacetic acid (1 mL) for 10 minutes and was concentrated. The residue was purified by reverse phase HPLC, eluted with 10-70% acetonitrile in 0.1% trifluoroacetic acid/water to afford the title compound. LCMS: 333.11 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 1.63-1.80 (m, 2H) 1.88 (d, 1H) 2.11 (d, 1H) 2.77-2.89 (m, 1H) 3.02-3.12 (m, 1H) 3.14-3.22 (m, 1H) 3.29 (d, 1H) 3.81 (s, 3H) 6.05 (d, 1H) 7.07 (d, 1H) 7.54 (s, 2H) 7.67 (s, 1H) 8.21 (d, 1H) 8.70 (d, 1H) 8.87 (s, 1H) 11.83 (s, 1H).

Workup

  1. concentrationwas concentrated
  2. customThe residue was purified by reverse phase HPLC
  3. washeluted with 10-70% acetonitrile in 0.1% trifluoroacetic acid/water

Sources & evidence

ORD record
ord-8ecb56646c664a2fb92a3a99bf31610f
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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