m-Formylbenzonitrile → HCID 178509712, compound

HRID 592017Notes

Reaction equation

HRID 592017 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.[C:21]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O)#[N:22].C([O-])(=O)C.[NH4+]>>[Cl: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][CH:30]=[C:23]([C:21]#[N:22])[CH:24]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 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 178509712HCID 178509712, compoundYield 70.3%

Procedure

In a similar fashion to Compound 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 (75.00 mg, 0.2553 mmol), 3-cyanobenzaldehyde (36.8 mg, 0.281 mmol), and Ammonium acetate (39.4 mg, 0.511 mmol) were reacted to produce 72.70 mg (63%) of the title compound. (300 MHz, DMSO-d6) 13.44 (s, 1H), 8.49 (s, 1H), 8.43 (d, J=8 Hz, 1H), 7.99 (s, 1H), 7.95 (d, J=8 Hz, 1H), 7.77 (m, 2H), 7.35 (d, J=9 Hz, 1H) 7.25 (s, 1H), 6.41 (m, 2H), 5.14 (t, J=17 Hz, 8.5 Hz, 1H), 2.91 (s, 1H), 2.81 (s, 1H), 2.63 (d, J=8 Hz, 1H), 2.23 (d, J=8 Hz, 1H), 1.39 (d, J=8 Hz, 1H). MS=405 (M+H), HPLC: 2.39 min. (G Method)

Sources & evidence

ORD record
ord-17afb99ca9d947b79cc014091e688b30
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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