3,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate → HCID 178454784, compound

HRID 1586233Notes

Reaction equation

HRID 1586233 reaction equation
[CH2:1]([CH:3]([C:24]([OH:26])=[O:25])[N:4]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=1)[CH3:2].[N+]([O-])(O)=O.C[C:32]1C=C(C)[N:34](C(N)=N)[N:33]=1>N1C=CC=CC=1>[CH2:1]([CH:3]([C:24]([OH:26])=[O:25])[N:4]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][CH:32]=[N:33][NH2:34])=[CH:21][CH:22]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 21217941HCID 21217941, compound

Product 1

HCID 178454784HCID 178454784, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Part E. A solution of ethyl N-[4-[4-aminophenyl]butyl]-N-[3-cyanophenyl]glycine (0.12 gm, 0.34 mmol) and 3,5-dimethylpyrazole-1-carboxamidine nitrate (0.103 gm, 0.51 mmol) in 10 mL pyridine was heated to 100° C. under a nitrogen atmosphere for 3 hrs. The reaction mixture was allowed to cool and was partitioned between ethyl acetate and water. The combined organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give the crude product. The product was purified by flash chromatography on silica gel eluting chloroform:methanol (v:v, 80:20) to give ethyl N-[4-[4-[(aminoiminomethyl)amino]phenyl]butyl]-N-[3-cyanophenyl]glycine 0.078 gm (58%) MS 394(M+H)+ 1 H NMR (CDCl3): 7.0(m, 10H), 6.8(m, 2H), 4.2(q, 2H), 4.0(s, 2H), 3.4(m, 2H), 2.7(m, 2H), 1.2(t, 3H).

Workup

  1. temperatureto cool
  2. customwas partitioned between ethyl acetate and water
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThe product was purified by flash chromatography on silica gel
  8. washeluting chloroform

Sources & evidence

ORD record
ord-a521fd4111cf4bf99e5f9a9dbb420594
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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