Triethylamine → [5-(3-Benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-(4-morpholin-4-yl-piperidin-1-yl)-methanone

HRID 1011904Notes

Reaction equation

HRID 1011904 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:20]([CH3:21])[N:19]=[C:18]([C:22](O)=[O:23])[C:17]=1[CH3:25].C(Cl)(=O)C(Cl)=O.[NH:32]1[CH2:37][CH2:36][CH:35]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[CH2:34][CH2:33]1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:20]([CH3:21])[N:19]=[C:18]([C:22]([N:32]2[CH2:37][CH2:36][CH:35]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)[CH2:34][CH2:33]2)=[O:23])[C:17]=1[CH3:25]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7957244-MorpholinopiperidineHCID 673142975-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 67313696[5-(3-Benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-(4-morpholin-4-yl-piperidin-1-yl)-methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A suspension of 0.080 g (0.24 mmol) of 5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid (Example 16C]) in 1.5 ml of CH2Cl2 was treated at RT with 1 drops of DMF. 0.02 ml (0.29 mmol, 1.2 eq) of oxalyl chloride in 0.5 ml CH2Cl2 were added dropwise and stirring was continued for 1 h. The solution was evaporated, redissolved in 1 ml of CH2Cl2, cooled (0° C.) and treated with a solution of 0.041 g (0.24 mmol, 1 eq) of 4-(piperidine-4-yl)-morpholine and 0.07 ml (0.48 mmol, 2 eq) of triethylamine in 0.5 ml of CH2Cl2. The reaction was stirred for 3 h at this temperature, then partitioned three times between EtOAc and aqueous saturated NaHCO3, dried over Na2SO4 and evaporated to give 0.134 g (quant.) of the title compound as light yellow foam. MS: 485.3 (MH+).

Workup

  1. customThe solution was evaporated
  2. dissolutionredissolved in 1 ml of CH2Cl2
  3. stirringThe reaction was stirred for 3 h at this temperature
  4. custompartitioned three times between EtOAc and aqueous saturated NaHCO3
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-8136f5571eaf49afb852a2424b3dded7
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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