Ammonium Acetate → HCID 178434019, compound

HRID 592025Notes

Reaction equation

HRID 592025 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.[CH3:21][N:22]1[C:26]([CH3:27])=[C:25]([CH:28]=O)[C:24]([CH3:30])=[N:23]1.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:28]([C:25]3[C:24]([CH3:30])=[N:23][N:22]([CH3:21])[C:26]=3[CH3:27])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 7365151,3,5-trimethyl-1H-pyrazole-4-carboxaldehydeHCID 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 178434019HCID 178434019, compoundYield 64%

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), 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde (33.7 mg, 0.244 mmol), and Ammonium acetate (34.2 mg, 0.444 mmol) were reacted to produce 63.66 mg (64%) of the title compound. (300 MHz, DMSO-d6) 12.46 (s, 1H), 7.99 (s, 1H), 7.70 (s, 1H), 7.19 (s, 1H), 7.93 (d, J=9 Hz, 1H), 6.32 (m, 1H), 6.25 (m, 1H), 5.23 (t, J=17 Hz, 9 Hz, 1H), 3.76 (s, 3H), 2.85 (s, 1H), 2.75 (s, 1H), 2.57 (d, J=9 Hz, 1H), 2.47 (s, 3H), 2.35 (s, 3H), 2.25 (d, J=8 Hz, 1H), 1.39 (d, J=8 Hz, 1H). MS=458 (M+H), HPLC: 2.0 min. (G Method)

Sources & evidence

ORD record
ord-394d69b3c9224911892c656cb496f428
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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