Triethylamine → (S)-3-[5-(2,5-Dihydro-1H-pyrrol-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile
Reaction equation
C(OC([N:8]1[CH2:12][CH:11]=[CH:10][C@H:9]1[C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[N:14]=1)=O)(C)(C)C.C(OC(N1CC=C[C@H]1C(O)=O)=O)(C)(C)C.ClC(OCC(C)C)=O.C(N(CC)CC)C.C(C1C=C(C=CC=1)C(NO)=N)#N>C1COCC1.CN(C=O)C>[NH:8]1[CH2:12][CH:11]=[CH:10][C@H:9]1[C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=2)[C:24]#[N:25])[N:14]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
(S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (372 mg, 42%, slightly impure) was prepared according to the procedure in Example 25 from (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester (557.8 mg, 2.62 mmol) with isobutyl chloroformate (0.36 mL, 2.77 mmol) and triethylamine (0.73 mL, 5.2 mmol) in THF (7.5 mL). Then 3-cyano-N-hydroxy-benzamidine (424 mg, 2.6 mmol) and DMF (7 mL) were added and the mixture was heated at 120° C. for 16 h. 1H-NMR (CDCl3) was consistent with the expected product and showing a mixture of rotomers due to the Boc protecting group.
Sources & evidence
- ORD record
- ord-fdbefcf0e0f64ddbb5e36be66ab81301
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074809B2
Reaction notes
Loading…