1-Boc-piperidine-3-carboxaldehyde → 3-[7-((1R,2R,3S,4S)-3-Carbamoyl-bicyclo[2.2.1]hept-5-en-2-ylamino)-6-chloro-3H-imidazo[4,5-b]pyridine-2-yl]-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([NH:31][C@@H:32]2[C@@H:37]3[CH2:38][C@@H:34]([CH:35]=[CH:36]3)[C@@H:33]2[C:39]([NH2:41])=[O:40])=[C:11]2[N:17]=[C:16]([C:18]3[CH:23]=CC(CN4CCOCC4)=C[CH:19]=3)[NH:15][C:12]2=[N:13][CH:14]=1.NC1C(N)=C(N[C@@H]2[C@@H]3C[C@@H](C=C3)[C@@H]2C(N)=O)C(Cl)=CN=1.[C:62]([O:66][C:67]([N:69]1CCC[CH:71](C=O)[CH2:70]1)=[O:68])([CH3:65])([CH3:64])[CH3:63]>>[C:62]([O:66][C:67]([N:69]1[CH2:70][CH2:71][CH2:19][CH:18]([C:16]2[NH:15][C:12]3=[N:13][CH:14]=[C:9]([Cl:8])[C:10]([NH:31][C@H:32]4[C@@H:33]([C:39](=[O:40])[NH2:41])[C@H:34]5[CH2:38][C@@H:37]4[CH:36]=[CH:35]5)=[C:11]3[N:17]=2)[CH2:23]1)=[O:68])([CH3:65])([CH3:64])[CH3:63]Participants
4
Reactant 3
Product 1
Procedure
In the same fashion as for Compound III, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 3-formyl-piperidine-1-carboxylic acid tert-butyl ester were reacted to produce the title compound (65%). 1H NMR (d-chloroform): 15.20 (br s, 1H), 8.42 (m, 1H), 7.83 (s, 1H), 6.45 (m, 1H), 6.38 (m, 1H), 5.90 (m, 1H), 5.64 (s, 1H), 5.25 (m, 1H), 4.03 (m, 1H), 2.80-3.25 (m, 5H), 2.62 (t, J=8 Hz, 1H), 2.39 (d, J=10 Hz, 2H), 1.32-2.00 (m, 14H). MS: 488.07 (M+H). HPLC retention time: 2.67 minutes (G Method).
Sources & evidence
- ORD record
- ord-898e4fdc0c634c3a809f79bee9ae7c78
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238656B2
Reaction notes
Loading…