2-Methoxybenzaldehyde → (1S,2S,3R,4R)-3-[6-Chloro-2-(2-methoxy-phenyl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HRID 591923Notes

Reaction equation

HRID 591923 reaction equation
FC(F)(F)[C:3](O)=[O:4].[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]=[CH:22][C:21](CN4CCOCC4)=[CH:20][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.COC1C=CC=CC=1C=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:19]=[CH:20][CH:21]=[CH:22][C:23]=3[O:4][CH3:3])[NH:15][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideHCID 178513995HCID 178513995, compound

Product 1

HCID 178489350(1S,2S,3R,4R)-3-[6-Chloro-2-(2-methoxy-phenyl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideYield 96%

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 2-methoxybenzaldehyde were reacted to produce the title compound (96%). 1H NMR (d-chloroform): 13.89 (br s, 1H) 8.31 (dd, J=1.8 Hz, 1H), 8.10 (d, J=9 Hz, 1H), 7.84 (s, 1H), 7.46 (m, 1H), 7.10 (t, J=8 Hz, 1H), 7.04 (d, J=8 Hz, 1H), 6.49 (m, 1H), 6.43 (m, 1H), 6.07 (br s, 1H), 5.60 (br s, 1H), 5.39 (t, J=8 Hz, 1H), 4.15 (s, 3H), 3.16 (s, 1H), 3.01 (s, 1H), 2.73 (d, J=9 Hz, 1H), 2.33 (d, J=9 Hz, 1H), 1.67 (d, J=9 Hz, 1H). MS: 411.04 (M+H). HPLC retention time: 2.58 minutes (G Method).

Sources & evidence

ORD record
ord-0b98981d7ccc48e79f53a6c529e7fc13
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

Loading…