Dimethylformamide → HCID 67296164, compound

HRID 2276855Notes

Reaction equation

HRID 2276855 reaction equation
CN(C)C=O.Cl[CH2:7][C:8]#[N:9].[C:10]1([C@H:20]([NH:22][C@H:23]2[CH2:27][CH2:26][C@@H:25]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[CH2:24]2)[CH3:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:10]1([C@H:20]([NH:22][C@H:23]2[CH2:27][CH2:26][C@@H:25]([C:28]3[CH:29]=[CH:30][C:31]([O:34][CH2:7][C:8]#[N:9])=[CH:32][CH:33]=3)[CH2:24]2)[CH3:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 59617435HCID 59617435, compound

Product 1

HCID 67296164HCID 67296164, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen stream, N,N-dimethylformamide (3 mL) and chloroacetonitrile (0.11 mL, 1.8 mmol) were added to 4-[(1R,3S)-3-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclopentyl]phenol (500 mg, 1.5 mmol) obtained in Example 10 (Step 3) and potassium carbonate (250 mg, 1.8 mmol), and the mixture was stirred for 5 days at room temperature. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue obtained was purified by column chromatography (NH silica; ethyl acetate/hexane:20/80-50/50) to give the title compound (382 mg, 68%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue obtained
  5. customwas purified by column chromatography (NH silica; ethyl acetate/hexane:20/80-50/50)

Sources & evidence

ORD record
ord-f25738b0158e45a28da3f7dfab8491d5
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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