4-Fluorobenzaldehyde → HCID 178513974, compound

HRID 592008Notes

Reaction equation

HRID 592008 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.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C([O-])(=O)C.[NH4+]>>[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:25]3[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 517165Ammonium AcetateHCID 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 178513974HCID 178513974, compoundYield 54.2%

Procedure

In a similar fashion to compound CXXV, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (100.00 mg, 0.29568 mmol), 4-Fluorobenzaldehyde (40.4 mg, 0.325 mmol), and Ammonium acetate (45.6 mg, 0.591 mmol) were reacted to yield 70.9 mg (54%) of the title compound. (300 MHz, DMSO-d6) 13.42 (s, 1H), 8.06 (s, 1H), 7.99 (d, J=8 Hz, 1H), 7.90 (d, J=11 Hz, 1H), 7.76 (s, 1H), 7.61 (m, 1H), 7.33 (m, 1H), 7.24 (m, 2H) 6.39 (s, 2H), 5.21 (t, J=17 Hz, 8.5 Hz, 1H), 2.89 (s, 1H), 2.78 (s, 1H), 2.63 (d, J=8 Hz, 1H), 2.24 (d, J=8 Hz, 1H), 1.39 (d, J=8 Hz, 1H). MS=444 (M+H).

Sources & evidence

ORD record
ord-6a767d8de5614f6f9d486c30d492e90a
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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