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

HRID 591918Notes

Reaction equation

HRID 591918 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]=[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.[N:62]1(C2C=CC(C=O)=CC=2)[CH2:67][CH2:66][O:65][CH2:64][CH2:63]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:23]=[CH:22][C:21]([N:62]4[CH2:67][CH2:66][O:65][CH2:64][CH2:63]4)=[CH:20][CH:19]=3)[NH:15][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 2913494-MorpholinobenzaldehydeHCID 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 178514000(1S,2S,3R,4R)-3-[6-Chloro-2-(4-morpholin-4-yl-phenyl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideYield 20%

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-morpholin-4-yl-benzaldehyde were reacted to produce the title compound (20%). 1H NMR (d-chloroform): 15.43 (br s, 1H), 8.06 (d, J=9 Hz, 1H), 8.00 (d, J=9 Hz, 2H), 7.77 (s, 1H), 7.02 (d, J=9 Hz, 2H), 6.50 (m, 1H), 6.42 (m, 1H), 5.91 (br s, 1H), 5.53 (br s, 1H), 5.40 (t, J=8 Hz, 1H), 3.90 (t, J=5 Hz, 4H), 3.30 (t, J=5 Hz, 4H), 3.17 (s, 1H), 3.04 (s, 1H), 2.68 (d, J=8 Hz, 1H), 2.38 (d, J=9 Hz, 1H), 1.67 (d, J=9 Hz, 1H). MS: 466.07 (M+H). HPLC retention time: 2.42 minutes (G Method).

Sources & evidence

ORD record
ord-50f2fdb695944cd0855c062804232f10
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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