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

HRID 591920Notes

Reaction equation

HRID 591920 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(C=O)=CC=1>>[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][C:21]([O:4][CH3:3])=[CH:22][CH:23]=3)[NH:15][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 312444-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 178488907(1S,2S,3R,4R)-3-[6-Chloro-2-(4-methoxy-phenyl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideYield 16%

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 4-methoxybenzaldehyde were reacted to produce the title compound (16%). 1H NMR (d-chloroform): 15.54 (br s, 1H) 8.23 (d, J=9 Hz, 1H), 8.06 (d, J=9 Hz, 2H), 7.79 (s, 1H), 7.06 (d, J=9 Hz, 2H), 6.51 (m, 1H), 6.42 (m, 1H), 5.86 (br s, 1H), 5.46 (br s, 1H), 5.39 (t, J=8 Hz, 1H), 3.91 (s, 3H), 3.17 (s, 1H), 3.05 (s, 1H), 2.68 (d, J=9 Hz, 1H), 2.33 (d, J=9 Hz, 1H), 1.68 (d, J=10 Hz, 1H). MS: 466.07 (M+H). HPLC retention time: 2.42 minutes (G Method).

Sources & evidence

ORD record
ord-c3b175b15cb04fe49f92ab6f39340ac2
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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