3-(Morpholinomethyl)benzaldehyde → (1S,2S,3R,4R)-3-[2-(3-Morpholin-4-ylmethyl-phenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HRID 591975Notes

Reaction equation

HRID 591975 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[CH:5]=[CH:4][N:3]=1.[N:20]1([CH2:26][C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=2)[CH:30]=O)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[N:20]1([CH2:26][C:27]2[CH:28]=[C:29]([C:30]3[NH:1][C:2]4=[N:3][CH:4]=[CH:5][C:6]([NH:9][C@@H:10]5[C@@H:15]6[CH2:16][C@@H:12]([CH:13]=[CH:14]6)[C@@H:11]5[C:17]([NH2:19])=[O:18])=[C:7]4[N:8]=3)[CH:32]=[CH:33][CH:34]=2)[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 71646033-(Morpholinomethyl)benzaldehydeHCID 117701640HCID 117701640, compound

Product 1

HCID 178514009(1S,2S,3R,4R)-3-[2-(3-Morpholin-4-ylmethyl-phenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideYield 34%

Procedure

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50.0 mg, 0.193 mmol) and 3-morpholin-4-ylmethyl-benzaldehyde (43.5 mg, 0.212 mmol) were reacted to produce 29 mg (34%) of the title compound. mp: 240-244° C., 1H NMR (300 MHz, DMSO-d6) 13.09 (s, 1H), 8.10 (s, 1H), 8.02 (d, J=8 Hz, 1H), 7.91 (d, J=8 Hz, 1H), 7.67 (s, 1H), 7.47 (t, J=8 Hz, 1H), 7.39 (m, 1H), 7.17 (s, 1H), 6.91 (m, 1H), 6.41 (d, J=8 Hz, 1H), 6.34 (s, 1H), 3.88 (br s, 1H), 3.60 (br s, 4H), 3.54 (s, 2H), 2.88 (s, 1H), 2.77 (s, 1H), 2.61 (d, J=8 Hz, 1H), 2.40 (s, 4H), 2.24 (d, J=8 Hz, 1H), 1.43 (d, J=8 Hz, 1H). MS: 445 (M+H), HPLC: 1.54 min (G method).

Sources & evidence

ORD record
ord-9500fa6e19eb4090a9814f061209012f
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

Loading…