3-Fluorobenzaldehyde → HCID 178513474, compound

HRID 592004Notes

Reaction equation

HRID 592004 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]([Cl: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+]>>[Cl:20][C:5]1[C:6]([NH:9][CH:10]2[CH:15]3[CH2:16][CH:12]([CH:13]=[CH:14]3)[CH: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 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178513474HCID 178513474, compoundYield 56%

Procedure

In a similar fashion compound to CXXV, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50.00 mg, 0.1702 mmol), 3-FC6H4CHO (23.2 mg, 0.187 mmol) and Ammonium acetate (26.2 mg, 0.340 mmol) were reacted to yield 37.94 mg (56%) of the title compound. (300 MHz, DMSO-d6) 13.40 (s, 1H), 7.99 (m, 2H), 7.91 (s, 1H), 7.78 (s, 1H), 7.60 (s, 1H), 7.29 (m, 3H), 6.39 (s, 2H), 5.15 (m, 1H), 2.90 (s, 1H), 2.80 (s, 1H), 2.62 (s, 1H), 2.26 (s, 1H), 1.38 (s, 1H). MS=398 (M+H), HPLC: 2.55 min. (G Method)

Sources & evidence

ORD record
ord-ba0bcacc956e496bbc1c6df0df6c09b9
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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