3-Chlorobenzaldehyde → HCID 178513967, compound

HRID 592015Notes

Reaction equation

HRID 592015 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.[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.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:25]([C:24]3[CH:27]=[CH:28][CH:29]=[C:22]([Cl:21])[CH:23]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 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 178513967HCID 178513967, compoundYield 53.2%

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 (86.35 mg, 0.2553 mmol), 3-Chlorobenzaldehyde (39.5 mg, 0.281 mmol) and Ammonium acetate (39.4 mg, 0.511 mmol) were reacted to produce 62.33 mg (53%) of the title compound. (300 MHz, DMSO-d6) 3.42 (s, 1H), 8.18 s, 1H), 8.09 (d, J=8 Hz, 1H), 8.05 (s, 1H), 7.76 (s, 1H), 7.62-7.53 (m, 2H), 7.27-7.22 (m, 2H), 6.38 (m, 2H), 5.19 (t, J=17 Hz, 9 Hz, 1H), 2.90 (s, 1H), 2.79 (s, 1H), 2.63 (d, J=8 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 1.40 (d, J=8 Hz, 1H). MS=460 (M+H), HPLC: 2.75 min. (G Method)

Sources & evidence

ORD record
ord-f50bc419301d48008fb9fcb133ac505e
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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