1-Methyl-1H-pyrazole-4-carbaldehyde → (1S,2S,3R,4R)-3-[6-Chloro-2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HRID 591922Notes

Reaction equation

HRID 591922 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]3C=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.[CH3:62][N:63]1[CH:67]=C(C=O)C=[N:64]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]=[N:64][N:63]([CH3:67])[CH:62]=3)[NH:15][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 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 178480121(1S,2S,3R,4R)-3-[6-Chloro-2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideYield 88%

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 1-Methyl-1H-pyrazole-4-carbaldehyde were reacted to produce the title compound (88%). 1H NMR (d-chloroform): 15.26 (br s, 1H) 8.26 (d, J=8 Hz, 1H), 8.04 (s, 1H), 8.02 (s, 1H), 7.78 (s, 1H), 6.45 (m, 1H), 6.41 (m, 1H), 5.99 (s, 1H), 5.70 (s, 1H), 5.31 (t, J=8 Hz, 1H), 4.02 (s, 3H), 3.16 (s, 1H), 3.00 (s, 1H), 2.68 (d, J=8 Hz, 1H), 2.29 (d, J=9 Hz, 1H), 1.66 (d, J=10 Hz, 1H). MS: 385.06 (M+H). HPLC retention time: 1.90 minutes (G Method).

Sources & evidence

ORD record
ord-e8c6fffd300c46839745bbf4f8134c6f
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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