Ethyl orthoformate → HCID 21880589, compound

HRID 899325Notes

Reaction equation

HRID 899325 reaction equation
[N:1]1([NH:7][C:8]([C:10]2[C:14]([NH2:15])=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[N:11]=2)=[O:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:30](OC(OCC)OCC)C>C1(C)C=CC=CC=1.O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[N:11]=[C:10]3[C:8](=[O:9])[N:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[CH:30]=[N:15][C:14]=23)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 58747011HCID 58747011, compound

Product 1

HCID 21880589HCID 21880589, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 4-amino-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid morpholin-4-ylamide (1-10A-1a, 200 mg, 0.46 mmol) and triethylorthoformate (116 microliters, 0.7 mmol) in toluene (2.5 ml) was heated at 100° C. for 0.45 h and at 120° C. for 2 h. The reaction mixture was cooled to room temperature, diluted with H2O, and extracted with EtOAc (2×). The combined organic extracts were washed with 1 M K2CO3 and saturated aqueous brine, dried, and concentrated under vacuum. The crude residue was purified via radial chromatography (1 mm plates, 50% EtOAc/hexanes as eluant) to give the desired product 10A-1 as an amorphous solid: MS 442.1 (M+1)+; 1H NMR (400 MHz, CDCl3) δ 7.99 (s, 1H), 7.53-7.50 (m, 1H), 7.47-7.39 (m, 3H), 7.35-7.28 (m, 4H), 4.25 (bm, 2H), 3.95 (bm, 2H), 3.75 (bm, 2H), 3.00 (bm, 2H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with 1 M K2CO3 and saturated aqueous brine
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe crude residue was purified via radial chromatography (1 mm plates, 50% EtOAc/hexanes as eluant)

Sources & evidence

ORD record
ord-329977f1301a42e6bd8e2225844ad473
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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