Trifluoroacetic acid → HCID 6914611, compound

HRID 2307771Notes

Reaction equation

HRID 2307771 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:30]C(=O)OC(C)(C)C)[CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[CH:26]=[N:25][CH:24]=[CH:23]4)[CH:19]=2)=[CH:2]1.C(O)(C(F)(F)F)=O>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH2:30])[CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[CH:26]=[N:25][CH:24]=[CH:23]4)[CH:19]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 91265468HCID 91265468, compound

Product 1

HCID 6914611HCID 6914611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 27B (0.125 g, 0.25 mmol) in dichloromethane (3 mL) at room temperature was treated with TFA (400 μL), stirred for 1 hour, and concentrated. The concentrate was azeotropically distilled with diethyl ether two times and the residue was purified by reverse phase HPLC on a C18 column with 0-100% CH3CN/H2O/0.1% TFA to provide the desired product as the di-trifluoroacetate salt (0.110 g, 70%). MS (ESI) m/e 395 (M+H)+; 1H NMR (DMSO-d6, 300 MHz) δ 11.02 (br s, 1H), 9.52 (s, 1H), 8.76 (d, J=3 Hz, 1H), 8.62 (d, J=8 Hz, 1H), 8.44-8.46 (m, 2H), 8.38 (d, J=9 Hz, 1H), 8.11-8.20 (m, 3H), 8.04-8.08 (m, 1H), 7.83-7.86 (m, 1H), 7.62 (d, J=9 Hz, 1H), 7.37-7.40 (m, 1H), 7.31 (d, J=3 Hz, 1H), 7.08-7.12 (m, 1H), 6.99-7.03 (m, 1H), 4.37-4.41 (m, 1H), 4.18-4.23 (m, 1H), 3.86-3.91 (m, 1H), 3.16-3.20 (m, 2H); Anal. Calcd for C25H22N4O.2TFA.H2O: C, 49.35; H, 3.61; N, 7.43; F, 22.67. Found: C, 49.04; H, 3.55; N, 7.42; F, 22.28.

Workup

  1. concentrationconcentrated
  2. distillationThe concentrate was azeotropically distilled with diethyl ether two times
  3. customthe residue was purified by reverse phase HPLC on a C18 column with 0-100% CH3CN/H2O/0.1% TFA

Sources & evidence

ORD record
ord-79c2c2a252664c0aa41b908c532c3b34
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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