Ammonium Acetate → HCID 178480123, compound

HRID 592059Notes

Reaction equation

HRID 592059 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[O:16][C@@H:12]([CH2:13][CH2:14]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[CH:26]=[C:25]([CH:27]=O)[CH:24]=[N:23]1.C([O-])(=O)C.[NH4+]>CCO>[Cl:20][C:5]1[C:6]([NH:9][C@@H:10]2[C@@H:15]3[O:16][C@@H:12]([CH2:13][CH2:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=[C:27]([C:25]3[CH:24]=[N:23][N:22]([CH3:21])[CH:26]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 89738581HCID 89738581, compound

Product 1

HCID 178480123HCID 178480123, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

(1S,2R,3S,4R)-3-(2,3-diamino-5-chloropyridin-4-ylamino)-7-oxabicyclo[2.2.1]heptane-2-carboxamide (17) (90 mg, 0.302 mmol), 1-methyl-1H-pyrazole-4-carbaldehyde (30 mg, 0.272 mmol) were taken in EtOH (15 ml) to which ammonium acetate (35 mg) was added and the reaction mixture was heated at 70° C. for 48 h. Crude LCMS showed the desired product along with trace of starting material. The reaction mixture was allowed to come to rt and the precipitated was filtered and washed well with hot ethanol to afford the desired product (70 mg, 41%) as a white solid. NMR: δ (1H, 400M Hz, DMSO-d6): 1.40-1.80 (4H, m), 2.92 (1H, d, J=8.4 Hz), 3.92 (3H, s), 4.28 (1H, s), 4.56 (1H, s), 5.40-5.55 (1H, m), 6.82 (1H, s), 7.14 (1H, s), 7.1 (1H, s), 7.86 (1H, s), 7.99 (1H, s), 8.23 (1H, s).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-c3d8b55d767c401b863c56839877a04f
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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