Ethyl chloroformate → HCID 67030874, compound

HRID 2405960Notes

Reaction equation

HRID 2405960 reaction equation
[CH3:1][C:2]([NH:10][C:11]([C:13]1[S:36][C:16]2[NH:17][N:18]=[C:19]([NH:20][C:21](=[O:35])[C:22]3[CH:27]=[CH:26][C:25]([CH2:28][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:24][CH:23]=3)[C:15]=2[CH:14]=1)=[O:12])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].C(N(C(C)C)CC)(C)C.Cl[C:47]([O:49][CH2:50][CH3:51])=[O:48]>C1COCC1>[CH2:50]([O:49][C:47]([N:17]1[C:16]2[S:36][C:13]([C:11](=[O:12])[NH:10][C:2]([CH3:1])([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH3:3])=[CH:14][C:15]=2[C:19]([NH:20][C:21](=[O:35])[C:22]2[CH:23]=[CH:24][C:25]([CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:26][CH:27]=2)=[N:18]1)=[O:48])[CH3:51]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 178457635HCID 178457635, compound

Product 1

HCID 67030874HCID 67030874, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-Piperidin-1-ylmethyl-benzoylamino)-1H-thieno[2,3-c]pyrazole-5-carboxylic acid (1-methyl-1-phenyl-ethyl)-amide (500 mg, 1 mmol) in anhydrous THF (20 mL), diisopropylethylamine (1.027 ml, 6 mmol) was added dropwise at room temperature. The reaction was stirred for 5 minutes, and then ethyl chloroformate (130 mg, 0.115 mL, 1.2 mmol) wais also added dropwise. After stirring for 1 hour, the solvent was evaporated, the crude taken up with dichloromethane washed thoroughly with water, brine and dried with sodium sulfate. After filtration and evaporation the crude was triturated with ethyl ether to give the title compound as white solid.

Workup

  1. stirringAfter stirring for 1 hour
  2. customthe solvent was evaporated
  3. washwashed thoroughly with water, brine
  4. dry with materialdried with sodium sulfate
  5. filtrationAfter filtration and evaporation the crude
  6. customwas triturated with ethyl ether

Sources & evidence

ORD record
ord-dc5d9291754e4a1faec41cc71e5050f4
Source dataset
uspto-grants-2014_08
Patent number
US08809337B2

Reaction notes

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