2-Chlorobenzaldehyde → HCID 178513965, compound

HRID 592022Notes

Reaction equation

HRID 592022 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:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=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:24]([C:23]3[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=3[Cl:21])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 69962-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 178513965HCID 178513965, compoundYield 50.4%

Procedure

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (75 mg, 0.22 mmol), 2-Chlorobenzaldehyde (34.3 mg, 0.244 mmol), and Ammonium acetate (34.2 mg, 0.444 mmol) were reacted to produce 50.82 mg (50%) of the title compound. (300 MHz, DMSO-d6) 13.16 (s, 1H), 8.07 (s, 1H), 7.84 (m, 1H), 7.72 (s, 1H), 7.64 (m, 1H), 7.52 (m, 2H), 7.20 (s, 1H), 7.14 (d, J=9 Hz, 1H), 6.29 (s, 2H), 5.21 (t, J=17 Hz, 8.5 Hz, 1H), 2.86 (s, 1H), 2.77 (s, 1H), 2.57 (d, J=8 Hz, 1H), 2.24 (d, J=8 Hz, 1H), 1.38 (d, J=8 Hz, 1H). MS=460 (M+H), HPLC: 2.46 min. (G Method)

Sources & evidence

ORD record
ord-f6d5bc34a03a4bc9aee4422b501d8a13
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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