1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 117840745, compound

HRID 714875Notes

Reaction equation

HRID 714875 reaction equation
[C:1]([C@@:3]1([CH2:25][CH3:26])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)[N:9]=2)[C:4]1=[O:24])#[N:2].Cl.[NH2:28][C:29]1([C:32]#[N:33])[CH2:31][CH2:30]1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)CC)C>[C:32]([C:29]1([NH:28][C:19](=[O:21])[C:18]2[CH:22]=[CH:23][C:15]([NH:14][C:10]3[N:9]=[C:8]([N:5]4[CH2:6][CH2:7][C@@:3]([C:1]#[N:2])([CH2:25][CH3:26])[C:4]4=[O:24])[CH:13]=[CH:12][N:11]=3)=[CH:16][CH:17]=2)[CH2:31][CH2:30]1)#[N:33]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 89863434HCID 89863434, compound

Product 1

HCID 117840745HCID 117840745, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-((4-((3R)-3-cyano-3-ethyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)benzoic acid (100 mg) obtained in Example 231 in N,N-dimethylformamide (2.0 mL) were added 1-aminocyclopropanecarbonitrile hydrochloride (31 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (46 mg), 1-hydroxybenzotriazole (40 mg) and triethylamine (56 μL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (38 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0229f96572144809b7403c546d39ce2a
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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