Ammonium Acetate → HCID 178480118, compound

HRID 592047Notes

Reaction equation

HRID 592047 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C:10]23[C:16]([CH3:18])([CH3:17])[C:13]([CH3:19])([CH2:14][CH2:15]2)[C:12](=[O:20])[CH2:11]3)[C:5]([Cl:21])=[CH:4][N:3]=1.[CH3:22][N:23]1[CH:27]=[C:26]([CH:28]=O)[CH:25]=[N:24]1.C([O-])(=O)C.[NH4+]>CCO>[Cl:21][C:5]1[C:6]([NH:9][C:10]23[C:16]([CH3:17])([CH3:18])[C:13]([CH3:19])([CH2:14][CH2:15]2)[C:12](=[O:20])[CH2:11]3)=[C:7]2[N:8]=[C:28]([C:26]3[CH:25]=[N:24][N:23]([CH3:22])[CH:27]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 89726037HCID 89726037, compound

Product 1

HCID 178480118HCID 178480118, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

4-(2,3-diamino-5-chloropyridin-4-ylamino)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (10) (380 mg, 1.23 mmol), 1-methyl-1H-pyrazole-4-carbaldehyde (135 mg, 1.23 mmol) were taken in EtOH (15 ml) to which ammonium acetate (112 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 ethanol to afford the desired product (478 mg, 25%) as an off white solid. NMR: δ (1H, 400M Hz, DMSO-d6): 0.90 (3H, s), 0.91 (3H, s), 1.09 (3H, s), 1.40-1.80 (3H, m), 2.30-2.60 (1H, m), 3.00-3.10 (1H, m), 3.51-3.70 (1H, m), 3.93 (3H, s), 5.36 (1H, s), 8.00 (1H, s), 8.04 (1H, s), 8.31 (1H, s), 13.09 (1H, s). LCMS (254 nm): [M+H]+ 399.00 (96.43%). HPLC: 254 nm (94.06%)

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-64334f5909784109939a75a3be86e877
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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