3-Furaldehyde → HCID 178513981, compound

HRID 591987Notes

Reaction equation

HRID 591987 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.[O:21]1[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22]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:26]([C:23]3[CH:24]=[CH:25][O:21][CH:22]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 103513-FuraldehydeHCID 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 178513981HCID 178513981, compoundYield 54%

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 3-Furaldehyde (15.6 mg, 0.163 mmol) were reacted to produce 33 mg (54%) of the title compound. mp: 231-232° C., 1H NMR (300 MHz, DMSO-d6): 13.1 (s, 1H), 8.31 (s, 1H), 8.00 (s, 1H), 7.84 (s, 1H), 7.74 (br s, 1H), 7.21 (s, 1H), 7.10 (d, J=8 Hz, 1H), 7.01 (s, 1H), 6.40 (br s, 1H), 6.33 (br s, 1H), 5.15 (t, J=8 Hz, 1H), 2.87 (s, 1H), 2.74 (s, 1H), 2.60 (d, J=8 Hz, 1H), 2.23 (d, J=8 Hz, 1H), 1.37 (d, J=8 Hz, 1H). MS: 414-416 (M+H), HPLC: 2.27 min (G method)

Sources & evidence

ORD record
ord-004c1c64b67a4758a92c0899d888433e
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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