Water → Pyrazinamide

HRID 1641420Notes

Reaction equation

HRID 1641420 reaction equation
CCN=C=[N:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:11])C.Cl.C1C=CC2N(O)N=[N:19][C:17]=2C=1.[OH2:23]>CN(C=O)C>[N:19]1[CH:17]=[CH:11][N:9]=[CH:8][C:7]=1[C:6]([NH2:5])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 1046PyrazinamideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from step 6 (140 mg, 0.45 mmol), EDC.HCl (128 mg, 0.67 mmol) and HOBt.H2O (102 mg, 0.67 mmol) in anhydrous DMF (25 mL) was stirred together at room temperature for 30 min. To this stirred mixture was added (R)-dibenzyl 2-aminosuccinate p-TsOH salt (213 mg, 0.44 mmol) followed by TEA (1 mL). The resulting mixture was stirred for 16 h thereafter. The reaction mixture was concentrated and partitioned with EtOAc and saturated sodium bicarbonate solution. The EtOAc layer was separated and washed with saturated sodium bicarbonate and brine, dried (Na2SO4), filtered and concentrated to afford 240 mg (88% yield) of the pyrazine amide as an orange foam: LCMS (15-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=8.76 min on 250 mm column, (M+H)+=610, (M+Na)+=632.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned with EtOAc and saturated sodium bicarbonate solution
  3. customThe EtOAc layer was separated
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0445c604090a44fa8a6816e5aef5722e
Source dataset
uspto-grants-2012_02
Patent number
US08115000B2

Reaction notes

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