Ethyl chloroformate → HCID 178480688, compound

HRID 1096160Notes

Reaction equation

HRID 1096160 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:27]=[CH:26][C:11]([C:12]([NH:14][C:15]3[C:16]4[CH:22]=[C:21]([C:23](O)=[O:24])[S:20][C:17]=4[NH:18][N:19]=3)=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.C(OC(Cl)=O)C.[CH3:43][C:44]([NH2:52])([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH3:45]>CN(C)C=O.ClCCl>[CH3:43][C:44]([NH:52][C:23]([C:21]1[S:20][C:17]2[NH:18][N:19]=[C:15]([NH:14][C:12](=[O:13])[C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)=[CH:27][CH:26]=3)[C:16]=2[CH:22]=1)=[O:24])([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH3:45]

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 68509CumylamineHCID 81531DiisopropylethylamineHCID 178480692HCID 178480692, compound

Product 1

HCID 178480688HCID 178480688, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled suspension of 3-{[4-(4-methylpiperazin-1-yl)benzoyl]amino}-1H-thieno[2,3-c]pyrazole-5-carboxylic acid (113 mg, 0.27 mmol) and N,N′-diisopropylethylamine (2.1 mmol, 0.38 mL) in 3 mL of N,N-dimethylformamide were added, dropwise, 0.154 mL of ethylchloroformate (1.6 mmol). After 20 minutes, 1-methyl-1-phenyl-ethylamine (0.302 mL, 2.1 mmol) was added to the obtained solution and the reaction mixture was allowed to warm to room temperature. After 16 hours, the reaction mixture was diluted with dichloromethane and washed with an aqueous solution of sodium bicarbonate. After solvent evaporation the residue was taken up with methyl alcohol (9 mL) and triethylamine (1 mL) and stirred at 40° C. for 2 hours. The reaction mixture was then evaporated to dryness to give an oil, which was purified by flash chromatography over silica gel, using dichloromethane/methanol/ammonia 7N solution in methyl alcohol (93:6:1) as eluent, to afford the title compound as a white solid (61 mg).

Workup

  1. additionwere added
  2. waitAfter 16 hours
  3. washwashed with an aqueous solution of sodium bicarbonate
  4. customAfter solvent evaporation the residue
  5. customThe reaction mixture was then evaporated to dryness
  6. customto give an oil, which
  7. customwas purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-8280cd57890740d298db42b25faf9734
Source dataset
uspto-grants-2012_03
Patent number
US08138217B2

Reaction notes

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