3-Fluorobenzaldehyde → HCID 178513969, compound

HRID 592007Notes

Reaction equation

HRID 592007 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:23]=[C:24]([CH:28]=O)[CH:25]=[CH:26][CH:27]=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:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([F:21])[CH:23]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 680093-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 178513969HCID 178513969, compoundYield 65%

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), 3-FC6H4CHO (40.4 mg, 0.325 mmol) and Ammonium acetate (45.6 mg, 0.591 mmol) were reacted to yield 84.7 mg (65%) of the title compound. (300 MHz, DMSO-d6) 13.33 (s, 1H), 8.18 (m, 2H), 8.04 (s, 1H), 7.75 (s, 1H), 7.41 (t, J=16.5 Hz, 8 Hz, 2H), 7.22 (s, 1H), 6.39 (d, J=15 Hz, 2H), 5.22 (t, J=17 Hz, 8.5 Hz, 1H), 2.89 (s, 1H), 2.78 (s, 1H), 2.62 (d, J=8 Hz, 1H), 2.24 (d, J=8 Hz, 1H), 1.39 (d, J=8 Hz, 1H). MS=444 (M+H), HPLC: 2.56 min. (G Method)

Sources & evidence

ORD record
ord-57f02fafc70c4ac2bb09338ff4bad9ab
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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