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

HRID 591942Notes

Reaction equation

HRID 591942 reaction equation
FC(F)(F)C(O)=O.ClC1C(N[C@@H]2[C@@H]3C[C@@H](C=C3)[C@@H]2C(N)=O)=C2N=C(C3C=CC(CN4CCOCC4)=CC=3)NC2=NC=1.[NH2:42][C:43]1[C:48]([NH2:49])=[C:47]([NH:50][C@@H:51]2[C@@H:56]3[CH2:57][C@@H:53]([CH:54]=[CH:55]3)[C@@H:52]2[C:58]([NH2:60])=[O:59])[C:46]([Cl:61])=[CH:45][N:44]=1.[CH3:62][O:63][C:64]1[CH:69]=[CH:68][N:67]=[CH:66][C:65]=1[CH:70]=O>>[Cl:61][C:46]1[C:47]([NH:50][C@@H:51]2[C@@H:56]3[CH2:57][C@@H:53]([CH:54]=[CH:55]3)[C@@H:52]2[C:58]([NH2:60])=[O:59])=[C:48]2[N:49]=[C:70]([C:65]3[CH:66]=[N:67][CH:68]=[CH:69][C:64]=3[O:63][CH3:62])[NH:42][C:43]2=[N:44][CH:45]=1

Participants

4

Reactant 3

HCID 113325033-Formyl-4-methoxypyridineHCID 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 178493110(1S,2S,3R,4R)-3-[6-Chloro-2-(4-methoxy-pyridin-3-yl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideYield 89%

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-methoxy-pyridine-3-carbaldehyde were reacted to produce the title compound (89%). 1H NMR (d-6 DMSO): 13.16 (br s, 1H), 9.19 (s, 1H), 8.81 (s, 1H), 8.10 (s, 1H), 7.83 (s, 1H), 7.70 (m, 2H), 7.28 (s, 1H), 6.40 (s, 1H), 6.38 (s, 1H), 5.10 (t, J=7 Hz, 1H), 4.21 (s, 3H), 2.92 (s, 1H), 2.85 (s, 1H), 2.63 (d, J=8 Hz, 1H), 2.23 (d, J=8 Hz, 1H), 1.41 (d, J=8 Hz, 1H). MS: 411.14 (M+H). HPLC retention time: 1.60 minutes (G Method)

Sources & evidence

ORD record
ord-15b24f0bea51447ba83ef2ff17d95457
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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