Trifluoroacetic acid → HCID 11338795, compound

HRID 2102313Notes

Reaction equation

HRID 2102313 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]2[C:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[N:22][N:23]=[C:17]2[CH:16]1[C:32]1[O:36][N:35]=[C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=2)[N:33]=1)=O)(C)(C)C>ClCCl>[Cl:43][C:39]1[CH:38]=[C:37]([C:34]2[N:33]=[C:32]([CH:16]3[NH:15][CH2:20][CH2:19][N:18]4[C:21]([C:24]5[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=5)=[N:22][N:23]=[C:17]34)[O:36][N:35]=2)[CH:42]=[CH:41][CH:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69003859HCID 69003859, compound

Product 1

HCID 11338795HCID 11338795, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of 8-[3-(3-chloro-phenyl) -[1,2,4]oxadiazol-5-yl]-3-(4-methoxy-phenyl)-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylic acid tert-butyl ester (72.5 mg, 0.14 mmol) in dichloromethane (1 mL) at 0° C. The reaction mixture was then diluted with dichloromethane, After 15 minutes, the reaction was warmed to room temperature and stirred for an additional hour. washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated. Purification was performed by flash column chromatography on silica gel using 85-90% ethyl acetate in hexanes to 2% ammonia in methanol in dichloromethane followed by trituration with diethyl ether to afford the titled compound (40.6 mg, 69%). 1H NMR (CDCl3) δ (ppm): 8.10 (m, 1H), 8.00 (m, 1H), 7.67 (m, 2H), 7.48 (m, 2H), 7.05 (m, 2H), 7.86 (m, 1H), 4.09 (m, 3H), 3.89 (s, 3H), 3.47 (m, 2H), 3.24 (m, 1H), 2.83 (bs, 1H).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification

Sources & evidence

ORD record
ord-26e6c7bcca3d44d89f05ffd3f4e2b449
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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