Triethylamine → HCID 66792736, compound

HRID 534875Notes

Reaction equation

HRID 534875 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:23])[CH2:18][CH2:19][C:20]([OH:22])=O)[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[CH:24]1([CH2:27][NH:28][S:29]([NH2:32])(=[O:31])=[O:30])[CH2:26][CH2:25]1.CC1C=CC=C([N+]([O-])=O)C=1C(OC(=O)C1C([N+]([O-])=O)=CC=CC=1C)=O.C(N(CC)CC)C>O.C(#N)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:23])[CH2:18][CH2:19][C:20]([NH:32][S:29](=[O:31])(=[O:30])[NH:28][CH2:27][CH:24]2[CH2:26][CH2:25]2)=[O:22])[CH2:13][CH2:12]1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 21041395HCID 21041395, compoundHCID 66750856HCID 66750856, compound

Product 1

HCID 66792736HCID 66792736, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-[4-(2-tert-butylphenyl)piperazin-1-yl]-4-oxobutanoic acid obtained in Example 53 (500 mg), N-(cyclopropylmethyl)sulfamide (248 mg), 2-methyl-6-nitrobenzoic anhydride (692 mg), N,N-dimethylaminopyridine (192 mg), triethylamine (0.656 mL), and acetonitrile (10 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (148 mg, 21%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-308fc3814ace4c45b19f40e6bdf8573d
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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