4-Methylmorpholine → HCID 74014514, compound

HRID 1168633Notes

Reaction equation

HRID 1168633 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=O)=[CH:5][CH:4]=1)=[O:2].Cl.[CH3:15][C:16]1([CH3:23])[CH2:20][CH2:19][CH2:18][CH:17]1[CH2:21][NH2:22].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[CH3:15][C:16]1([CH3:23])[CH2:20][CH2:19][CH2:18][CH:17]1[CH2:21][NH:22][C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 118207147HCID 118207147, compound

Product 1

HCID 74014514HCID 74014514, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of 4-formylcinnamic acid (345 mg, 1.96 mmol) and 2,2-dimethylcyclopentylmethylamine, hydrochloride (321 mg, 1.96 mmol; title B compound of Example 1) in DMF (5 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (954 mg, 2.16 mmol) and N-methylmorpholine (0.47 mL, 4.31 mmol). The cooling bath was removed and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane and washed with 1 N HCl and saturated NaHCO3 solution. The organic layer was dried (MgSO4) and concentrated in vacuo to yield a light amber gum. MS: (ESI), (M+H)+ 286.

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction mixture was diluted with dichloromethane
  3. washwashed with 1 N HCl and saturated NaHCO3 solution
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a light amber gum

Sources & evidence

ORD record
ord-2d9205d8854c4c10b5e8c9135940a370
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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