Pyridine → HCID 178511072, compound

HRID 1713762Notes

Reaction equation

HRID 1713762 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH2:14][C:15](=O)[CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]3[O:33][C:34]([NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[F:44])=[N:35][N:36]=3)=[O:31])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1.N1C=CC=CC=1>C(Cl)Cl>[C:15]([CH2:16][C@H:17]1[CH2:18][CH2:19][C@H:20]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30]([C:32]3[O:33][C:34]([NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[F:44])=[N:35][N:36]=3)=[O:31])=[CH:27][CH:28]=2)[CH2:21][CH2:22]1)#[N:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 178513914HCID 178513914, compound

Product 1

HCID 178511072HCID 178511072, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic anhydride 0.042 mL, 0.05 mmol) was added to a stirred solution of N-{4-[trans-4-(2-amino-2-oxoethyl)cyclohexyl]phenyl}-5-[(2-fluorophenyl)amino]-1,3,4-oxadiazole-2-carboxamide (Example 516) (20 mg, 0.05 mmol) and pyridine (90 uL, 0.11 mmol) in DCM (2 mL). After 15 minutes DCM (10 mL) was added and the reaction mixture was washed sequentially with 1M HCl (5 mL), water (10 mL) and 10% ammonium hydroxide solution (5 mL) then dried and concentrated under reduced pressure to give the title compound (18 mg, 95%) as a solid; 1H NMR δ 1.13-1.30 (m, 3H), 1.40-1.54 (m, 2H), 1.60-1.75 (m, 1H), 1.76-1.92 (m, 5H), 2.40-2.50 (m, 1H), 7.10-7.19 (m, 1H), 7.20-7.35 (m, 4H), 7.68 (d, 2H), 8.03 (t, 1H), 10.75 (s, 1H), 10.93 (s, 1H); MS m/e MH+ 420.

Workup

  1. washthe reaction mixture was washed sequentially with 1M HCl (5 mL), water (10 mL) and 10% ammonium hydroxide solution (5 mL)
  2. customthen dried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e828f39cbfa949868340be0f55cf99de
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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