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

HRID 591982Notes

Reaction equation

HRID 591982 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])[C:5]([Br:20])=[CH:4][N:3]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][C:24]=1[CH:29]=O>>[Br:20][C:5]1[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])=[C:7]2[N:8]=[C:29]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][C:23]=3[O:22][CH3:21])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 113325033-Formyl-4-methoxypyridineHCID 117701905(1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178493109(1S,2S,3R,4R)-3-[6-Bromo-2-(4-methoxy-pyridin-3-yl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideYield 43%

Procedure

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50 mg, 0.148 mmol) and 4-Methoxy-pyridine-3-carbaldehyde (22.3 mg, 0.163) were reacted to produce 29 mg (43%) of the title compound. mp: 160° C., 1H NMR (300 MHz, DMSO-d6): 12.69 (s, 1H), 9.11 (s, 1H), 8.54 (d, J=8 Hz, 1H), 8.07 (s, 1H), 7.74 (s, 1H), 7.27 (d, J=8 Hz, 1H), 7.21 (s, 1H), 7.17 (d, J=9 Hz, 1H), 6.35 (s, 2H), 5.26 (t, J=8 Hz, 1H), 4.02 (s, 3H), 3.38 (q, J=8 Hz, 1H), 3.32 (s, 1H), 2.89 (s, 1H), 2.78 (s, 1H), 2.63 (d, J=8 Hz, 1H), 2.26 (d, J=8 Hz, 1H), 1.40 (d, J=8 Hz, 1H), 1.09 (t, J=8 Hz, 1H). MS: 455, 457 (M+H), HPLC: 1.64 min (G method).

Sources & evidence

ORD record
ord-1610db295c9046c799059b3003d12b22
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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