Triethylamine → HCID 117702799, compound

HRID 873825Notes

Reaction equation

HRID 873825 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[C:10]([CH3:22])=[N:11][N:12]([CH:19]3[CH2:21][CH2:20]3)[C:13]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.C(N(CC)CC)C.O(S(C)(=O)=O)S(C)(=O)=O.[CH3:40][O:41][C:42]1[CH:49]=[CH:48][C:45]([CH2:46][NH2:47])=[CH:44][CH:43]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:47][CH2:46][C:45]2[CH:48]=[CH:49][C:42]([O:41][CH3:40])=[CH:43][CH:44]=2)[C:9]2[C:10]([CH3:22])=[N:11][N:12]([CH:19]3[CH2:21][CH2:20]3)[C:13]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 81560Methanesulfonic anhydrideHCID 117702856HCID 117702856, compound

Product 1

HCID 117702799HCID 117702799, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylate (Step 23.5) (2.12 g, 6.33 mmol) and triethylamine (4.41 mL, 31.7 mmol) in CH2Cl2 (4 mL) under Ar was added Ms2O (2.206 g, 12.66 mmol) at −10° C. The reaction mixture was stirred for 30 min at this temperature. 4-Methoxybenzylamine (0.827 ml, 6.33 mmol) was added at 30° C. After 15 h at rt, the reaction mixture was quenched with a saturated aqueous solution of NaHCO3 (100 mL), and extracted with CH2Cl2 (2×100 mL). The combined organic layers were washed with a saturated aqueous solution of NaHCO3 (100 mL), dried (Na2SO4) and evaporated. The crude material was purified by silica gel column chromatography (Hex/EtOAc 5-20%) to afford the title product (2.22 g, 4.89 mmol, 77% yield) as a colorless oil. tR: 1.12 min (LC-MS 2); ESI-MS: 454 [M+H]+ (LC-MS 2); Rf=0.85 (hexane/EtOAc 1:1).

Workup

  1. waitAfter 15 h at rt
  2. customthe reaction mixture was quenched with a saturated aqueous solution of NaHCO3 (100 mL)
  3. extractionextracted with CH2Cl2 (2×100 mL)
  4. washThe combined organic layers were washed with a saturated aqueous solution of NaHCO3 (100 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude material was purified by silica gel column chromatography (Hex/EtOAc 5-20%)

Sources & evidence

ORD record
ord-c74d969cd25744e9974984beb89a7c93
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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