Triethylamine → HCID 178458316, compound

HRID 1890802Notes

Reaction equation

HRID 1890802 reaction equation
[C:1]([N:3]=[C:4]([NH:15][C:16]12[CH2:23][CH2:22][C:19]([C:24]([NH2:26])=O)([CH2:20][CH2:21]1)[CH2:18][CH2:17]2)[C:5]([CH3:14])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:6])#[N:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:1]([N:3]=[C:4]([NH:15][C:16]12[CH2:21][CH2:20][C:19]([C:24]#[N:26])([CH2:18][CH2:17]1)[CH2:22][CH2:23]2)[C:5]([CH3:14])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:6])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 178458318HCID 178458318, compound

Product 1

HCID 178458316HCID 178458316, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 82 (70 mg, 0.2 mmol) and triethylamine (120 mg, 1.2 mmol) in dichloromethane cooled in an ice bath was added trifluoroacetic anhydride (125 mg, 0.6 mmol) dropwise. After addition was complete, the mixture was stirred overnight at room temperature. After removal of the solvent, the residue was purified by preparative reverse phase HPLC [Waters 2767; Benetnach 10-C18 20×250 mm, 10 μm; 35-85% acetonitrile/water (0.05% trifluoroacetic acid), 30 mL/minute; detection at 214 and 254 nm] to give the titled compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.33 (t, J=7.85 Hz, 2H), 7.19 (t, J=7.4 Hz, 1H), 7.01 (s, 1H), 6.91 (d, J=7.6 Hz, 2H), 2.01˜2.08 (m, 12H), 1.69 (s, 6H); LCMS (ESI+) m/z 337.7 (M+H)+.

Workup

  1. additionAfter addition
  2. customAfter removal of the solvent
  3. customthe residue was purified by preparative reverse phase HPLC [Waters 2767; Benetnach 10-C18 20×250 mm, 10 μm; 35-85% acetonitrile/water (0.05% trifluoroacetic acid), 30 mL/minute; detection at 214 and 254 nm]

Sources & evidence

ORD record
ord-c959245bfef94e579ec2a056ffb95beb
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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