4-(4-Methylpiperazin-1-yl)benzaldehyde → (1S,2S,3R,4R)-3-{2-[4-(4-Methyl-piperazin-1-yl)-phenyl]-3H-imidazo[4,5-b]pyridin-7-ylamino}-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HRID 591972Notes

Reaction equation

HRID 591972 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.[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=2)[CH2:23][CH2:22]1>>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:34]=[CH:33][C:30]([C:31]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:29][CH:28]=2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 117701640(1S,2S,3R,4R)-3-(2,3-Diamino-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178480653(1S,2S,3R,4R)-3-{2-[4-(4-Methyl-piperazin-1-yl)-phenyl]-3H-imidazo[4,5-b]pyridin-7-ylamino}-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideYield 19%

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 4-(4-methyl-piperazin-1-yl)-benzaldehyde (43.3 mg, 0.212 mmol) were reacted to produce 16 mg (19%) of the title compound. mp: 220-222° C., 1H NMR (300 MHz, DMSO-d6): 12.81 (s, 1H), 7.98 (d, J=8 Hz, 2H), 7.85 (d, J=5 Hz, 1H), 7.66 (s, 1H), 7.16 (s, 1H), 7.04 (d, J=8 Hz, 2H), 6.75 (m, 1H), 6.37 (d, J=8 Hz, 1H), 6.33 (s, 2H), 3.88 (br s, 1H), 3.32 (s, 6H), 2.88 (s, 1H), 2.75 (s, 1H), 2.60 (d, J=8 Hz, 1H), 2.45 (br s, 4H), 1.42 (d, J=8 Hz, 1H). MS: 444 (M+H), HPLC: 1.57 min (G method).

Sources & evidence

ORD record
ord-af0a3810cbba4beeb20530dca4606ff0
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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