Ammonium Acetate → HCID 178434020, compound

HRID 592024Notes

Reaction equation

HRID 592024 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.[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+]>>[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: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 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 178434020HCID 178434020, compoundYield 37%

Procedure

In a similar fashion to Compound LXXXVII, (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), 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde (38.8 mg, 0.281 mmol), and Ammonium acetate (39.4 mg, 0.511 mmol) were reacted to produce 36.49 mg (37%) of the title compound. (300 MHz, DMSO-d6) 12.47 (s, 1H), 7.91 (s, 1H), 7.72 (s, 1H), 7.21 (s, 1H), 7.00 (d, J=9 Hz, 1H), 6.32 (m, 1H), 6.26 (m, 1H), 5.17 (t, J=17 Hz, 9 Hz, 1H), 3.73 (s, 3H), 2.85 (s, 1H), 2.77 (s, 1H), 2.57 (d, J=8 Hz, 1H), 2.47 (s, 3H), 2.35 (s, 3H), 2.24 (d, J=8 Hz, 1H), 1.38 (d, J=8 Hz, 1H). MS=412 (M+H), HPLC: 1.97 min. (G Method)

Sources & evidence

ORD record
ord-9478010bf9c54e48894f561b645e1820
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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