Trifluoroacetic acid → HCID 59471665, compound

HRID 78665Notes

Reaction equation

HRID 78665 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]([C:23]1[C:28]([C:29]2[O:30][C:31]([C:34]3[CH:39]=[CH:38][C:37]([CH2:40][NH:41][CH3:42])=[CH:36][C:35]=3[O:43][CH3:44])=[N:32][N:33]=2)=[N:27][C:26]([C:45]2[CH:50]=[CH:49][C:48]([S:51]([CH:54]([CH3:56])[CH3:55])(=[O:53])=[O:52])=[CH:47][CH:46]=2)=[CH:25][N:24]=1)C(=O)OC(C)(C)C)=O)(C)(C)C>C(Cl)Cl>[CH:54]([S:51]([C:48]1[CH:47]=[CH:46][C:45]([C:26]2[N:27]=[C:28]([C:29]3[O:30][C:31]([C:34]4[CH:39]=[CH:38][C:37]([CH2:40][NH:41][CH3:42])=[CH:36][C:35]=4[O:43][CH3:44])=[N:32][N:33]=3)[C:23]([NH2:15])=[N:24][CH:25]=2)=[CH:50][CH:49]=1)(=[O:53])=[O:52])([CH3:56])[CH3:55]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59472394HCID 59472394, compound

Product 1

HCID 59471665HCID 59471665, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (393.7 mg, 266.0 μL, 3.453 mmol) was added to a solution of tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-[5-[2-methoxy-4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]carbamate (80 mg, 0.1151 mmol) CH2Cl2 (10 mL). The resulting mixture was stirred at room temperature for 1 h, and then concentrated in vacuo to leave an oil. The oil was re-dissolved in CH2Cl2 (10 ml), and evaporated to dryness. The residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3 CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound as a yellow solid (27.1 mg, 39%); 1H NMR (400 MHz, DMSO) d 1.3 (d, 6H), 2.65-2.7 (m, 3H), 3.4-3.5 (m, 1H), 4.0 (s, 3H), 4.25-4.3 (m, 2H), 7.25 (d, 1H), 7.5 (s, 1H), 8.0 (d, 2H), 8.1 (d, 1H), 8.38 (d, 2H), 8.92 (br s, 2H) and 9.1 (s, 1H) ppm; MS (ES+) 495.3

Workup

  1. concentrationconcentrated in vacuo
  2. customto leave an oil
  3. customevaporated to dryness
  4. customThe residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3 CN) over 16 minutes at 25 mL/min]
  5. customThe fractions were collected
  6. customfreeze-dried

Sources & evidence

ORD record
ord-097c5e5d3a58499cbf203968626190ff
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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