2-Methoxypyridine-3-carbaldehyde → HCID 178494112, compound

HRID 591980Notes

Reaction equation

HRID 591980 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[C:28]([CH:29]=O)=[CH:27][CH:26]=[CH:25][N:24]=1>>[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:28]3[C:23]([O:22][CH3:21])=[N:24][CH:25]=[CH:26][CH:27]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 125333912-Methoxypyridine-3-carbaldehydeHCID 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 178494112HCID 178494112, compoundYield 64%

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 2-Methoxy-pyridine-3-carbaldehyde (22.3 mg, 0.163 mmol) were reacted to produce 43 mg (64%) of the title compound. mp: 201° C., 1H NMR (300 MHz, DMSO-d6): 12.64 (s, 1H), 8.45 (d, J=8 Hz, 1H), 8.32 (s, 1H), 8.07 (s, 1H), 7.75 (s, 1H), 7.22 (m, 2H), 7.17 (d, J=8 Hz, 1H), 6.39 (s, 1H), 6.36 (s, 1H), 5.23 (t, J=8 Hz, 1H), 4.05 (s, 3H), 2.89 (s, 1H), 2.78 (s, 1H), 2.62 (d, J=8 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 1.39 (d, J=8 Hz, 1H). MS: 455, 457 (M+H), HPLC: 2.39 min (G method).

Sources & evidence

ORD record
ord-e625341f59874227ab8b001e8ad5c770
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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