3-Chlorobenzaldehyde → HCID 178513988, compound

HRID 592013Notes

Reaction equation

HRID 592013 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.[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.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: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 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 178513988HCID 178513988, compoundYield 30%

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-Chlorobenzaldehyde (39.5 mg, 0.281 mmol), and Ammonium acetate (39.4 mg, 0.511 mmol) were reacted to produce 31.23 mg (30%) of the title compound. (300 MHz, DMSO-d6) 13.42 (s, 1H), 8.19 (s, 1H), 8.10 (d, J=8 Hz, 1H), 7.98 (s, 1H), 7.78 (s, 1H), 7.62-7.53 (m, 2H), 7.32 (d, J=9 Hz, 1H), 7.25 (s, 1H), 6.39 (s, 2H), 5.18 (t, J=17 Hz, 9 Hz, 1H), 2.87 (s, 1H), 2.91 (s, 1H), 2.81 (d, J=8 Hz, 1H), 2.63 (d, J=8 Hz, 1H), 2.23 (d, J=8 Hz, 1H), 1.38 (d, J=8 Hz, 1H). MS=414 (M+H), HPLC: 2.73 min. (G Method)

Sources & evidence

ORD record
ord-0a4baded88a34753aacfd326801f468b
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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