Hydrochloric Acid → HCID 178509156, compound

HRID 2095167Notes

Reaction equation

HRID 2095167 reaction equation
[NH2:1][CH2:2][C:3]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:5]([NH2:8])=[N:6][N:7]=1.C(N(CC)CC)C.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH:27]=[CH:26]1.Cl>CN(C=O)C.C(OCC)(=O)C>[NH2:8][C:5]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:3]([CH2:2][NH:1][C:25]([CH:26]=[CH:27][C:28]([OH:30])=[O:29])=[O:31])=[N:7][N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 8471TriethylamineHCID 178510679HCID 178510679, compound

Product 1

HCID 178509156HCID 178509156, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5-Aminomethyl-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (60 mg, 0.25 mmole) was dissolved in 3 mL of anhydrous DMF. To this solution was added triethylamine (0.51 mmole, 52 mg) and then a solution of maleic anhydride (30.2 mg, 0.31 mmole) in 1 mL of DMF. The reaction mixture was stirred at ambient temperature for 30 minutes and then worked up by the addition of saline and ethyl acetate. The mixture was acidified with 1 mL of 1.5 M HCl. The aqueous phase was extracted with ethyl acetate. The combined organic layer was washed with saline three times and dried over anhydrous MgSO4. The solution was then filtered, concentrated and purified by preparative TLC (CH2Cl2:MeOH:trace acetic acid=6:1) to yield 58 mg of the title compound as a yellow powder. MS (m/z, ES−): 331 (M−1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) □δ 11.90 (br s, 1H), 7.35-7.70 (m, 3H), 7.30 (br s, 2H), 6.12 (d, 1H), 5.70 (d, 1H), 4.52 (s, 2H).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washThe combined organic layer was washed with saline three times
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationThe solution was then filtered
  5. concentrationconcentrated
  6. custompurified by preparative TLC (CH2Cl2:MeOH:trace acetic acid=6:1)

Sources & evidence

ORD record
ord-d8b7a0bf981c4e2f843c281d63418d9e
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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