Acetonitrile → Trifluoroacetate

HRID 1034968Notes

Reaction equation

HRID 1034968 reaction equation
[CH:1]1([C:4]2[C:16]3[C:15]4[CH2:14][CH2:13][N:12](C(OCC5C=CC=CC=5)=O)[CH2:11][C:10]=4[C:9](=[O:27])[NH:8][C:7]=3[N:6]([CH3:28])[N:5]=2)[CH2:3][CH2:2]1.C(#N)C.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>>[CH:1]1([C:4]2[C:16]3[C:15]4[CH2:14][CH2:13][NH:12][CH2:11][C:10]=4[C:9](=[O:27])[NH:8][C:7]=3[N:6]([CH3:28])[N:5]=2)[CH2:3][CH2:2]1.[F:32][C:33]([F:38])([F:37])[C:34]([O-:36])=[O:35]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 135948812HCID 135948812, compound

Product 2

HCID 84468TrifluoroacetateHCID 136358079HCID 136358079, compound

Procedure

A solution of Example 66A (180 mg, 0.48 mmol) in trifluoroacetic acid (5 mL) was heated at 50° C. for 16 h. After cooling, acetonitrile was added and the mixture concentrated on a rotary evaporator. The residue was separated by HPLC (Zorbax C-18, 0.1% TFA/CH3CN/H2O) to provide the title product as trifluoroacetate salt. This product was treated with 1.0 M solution of HCl in ether to yield the HCl salt. Yield: 92 mg (60%). MS (DCI/NH3) m/z 245 (M+H)+; 1H NMR (500 MHz, DMSO-d6): δ 0.77-0.85 (m, 2H), 0.86-0.92 (m, 2H), 2.04-2.17 (m, 1H), 3.24-3.32 (m, 2H), 3.33-3.41 (m, 2H), 3.74 (s, 3H), 3.84-3.96 (m, 2H), 5.27 (br s, 1H), 9.64 (br s, 1H). Anal. Calcd for C13H16N4O.2.1HCl: C, 48.91; H, 5.69; N, 17.46. Found: C, 48.91; H, 5.88; N, 17.11.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture concentrated on a rotary evaporator
  3. customThe residue was separated by HPLC (Zorbax C-18, 0.1% TFA/CH3CN/H2O)

Sources & evidence

ORD record
ord-3404fc0f4b754c809074b525d84fefda
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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