Acetic Acid → HCID 178476698, compound

HRID 2054408Notes

Reaction equation

HRID 2054408 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Cl.C(O[CH:11]=[NH:12])C.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:21]=[C:22]([NH2:25])[NH:23][N:24]=1.[C:26]([OH:29])(=[O:28])[CH3:27]>C(Cl)Cl>[C:26]([OH:29])(=[O:28])[CH3:27].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:21]=[C:22]([NH:25][CH:11]=[NH:12])[NH:23][N:24]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 10340Sodium CarbonateHCID 12578842Ethyl formimidate hydrochlorideHCID 178507276HCID 178507276, compound

Product 1

HCID 178476698HCID 178476698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a vigorously stirred solution of saturated aqueous Na2CO3 (50 mL) and methylene chloride (50 ml) was added solid ethylformimidate hydrochloride salt (8.98 g, 82 mol). After stirring for several minutes the aqueous layer was separated and extracted with additional methylene chloride (3×50 ml). The combined organic layers were dried (MgSO4) and filtered. To the stirred solution was added 5-(2-chlorophenyl)-2H-pyrazol-3-ylamine (I-3A-9a; 5.27 g, 27 mmol) in methylene chloride (50 mL) and then glacial acetic acid (2.67 ml, 46.6 mmol), dropwise. A cloudy precipitate began to form as the acetic acid was added. After stirring overnight, the solids were collected by vacuum filtration, washed with methylene chloride, and then dried, in vacuo, to give intermediate I-3A-9b, contaminated with ˜25% of the corresponding dimer (MW=396; 2 pyrazoles+1 formamidine), as a solid (5.7 g, 75%): +APcI MS (M+1) 221.1; 1H NMR (400 MHz, CD3OD) δ 8.02 (s, 1H), 7.62-7.30 (m, 4H), 6.48 (s, 1H), 1.92 (s, 3H).

Workup

  1. customwas separated
  2. extractionextracted with additional methylene chloride (3×50 ml)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. additionwas added
  6. stirringAfter stirring overnight
  7. filtrationthe solids were collected by vacuum filtration
  8. washwashed with methylene chloride
  9. customdried, in vacuo
  10. customto give intermediate I-3A-9b

Sources & evidence

ORD record
ord-0da4159b778f48e98ec05757f22104b4
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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