Triethylamine → HCID 59346938, compound

HRID 20577Notes

Reaction equation

HRID 20577 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][C@H:19]([CH3:23])[CH2:20][O:21][CH3:22])[CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:30][N:31]1[CH:35]=[CH:34][C:33]([NH2:36])=[N:32]1.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][C@H:19]([CH3:23])[CH2:20][O:21][CH3:22])[CH:17]=1)[C:12]([NH:36][C:33]1[CH:34]=[CH:35][N:31]([CH3:30])[N:32]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1372541-Methyl-3-aminopyrazoleHCID 593469053-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoic acid

Product 1

HCID 59346938HCID 59346938, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

DMF (2 drops) was added to a solution of 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoic acid (3.79 g, 0.012 mol) and oxalyl chloride (1.25 mL, 0.015 mol) in DCM (60 mL) and stirred for 3 hours, following which the organics were removed in vacuo. The crude material was dissolved in DCM (30 mL) and slowly added, at 0° C., to a stirred suspension of 1-methyl-1H-pyrazol-3-amine (1.22 g, 0.013 mol) and triethylamine (3.5 mL, 0.025 mol) in DCM (30 mL). The mixture was stirred at ambient temperature for 24 hours and the organics evaporated in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with 1M aqueous hydrochloric acid (50 mL) and brine (50 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with a 50% ethyl acetate in isohexane, to give the desired compound. (4.23 g).

Workup

  1. customorganics were removed in vacuo
  2. dissolutionThe crude material was dissolved in DCM (30 mL)
  3. stirringThe mixture was stirred at ambient temperature for 24 hours
  4. customthe organics evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  6. washwashed with 1M aqueous hydrochloric acid (50 mL) and brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto give the crude product which
  11. customwas chromatographed on silica
  12. washeluting with a 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-c62a4155cf324b8d838b8d7b448f4108
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

Loading…