5-Methylfurfural → HCID 178423933, compound

HRID 591989Notes

Reaction equation

HRID 591989 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][C:22]1[O:26][C:25]([CH:27]=O)=[CH:24][CH:23]=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:27]([C:25]3[O:26][C:22]([CH3:21])=[CH:23][CH:24]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 120975-MethylfurfuralHCID 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 178423933HCID 178423933, compoundYield 30%

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 5-Methyl-2-furancarboxaldehyde (17.9 mg, 0.163 mmol) were reacted to produce 19 mg (30%) of the title compound. mp: 200-201° C., 1H NMR (300 MHz, DMSO-d6): 13.17 (s, 1H), 8.00 (s, 1H), 7.74 (s, 1H), 7.20 (s, 1H), 7.06 (s, 1H), 6.36 (s, 1H), 6.33 (s, 1H), 5.16 (t, J=8 Hz, 1H), 3.32 (s, 1H), 2.87 (s, 1H), 2.73 (s, 1H), 2.60 (d, J=8 Hz, 1H), 2.40 (s, 3H), 2.23 (d, J=8 Hz, 1H), 1.37 (d, J=8 Hz, 1H). MS: 428, 430 (M+H), HPLC: 2.39 (G method).

Sources & evidence

ORD record
ord-73f7a04bcfa741698fd4f07f401b4697
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

Loading…