4-Methylmorpholine → HCID 76578010, compound

HRID 910412Notes

Reaction equation

HRID 910412 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][O:7][CH2:8][CH:9]2[C:13](=[O:14])[N:12]([CH:15]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:18])=O)[C:11](=[O:22])[NH:10]2)=[CH:4][CH:3]=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:53]([O:60][NH2:61])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.Cl>CN(C=O)C>[CH2:53]([O:60][NH:61][C:16](=[O:18])[CH:15]([N:12]1[C:13](=[O:14])[CH:9]([CH2:8][O:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:24][CH:23]=2)[NH:10][C:11]1=[O:22])[CH:19]([CH3:21])[CH3:20])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 66660973HCID 66660973, compound

Product 1

HCID 76578010HCID 76578010, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of the compound obtained in step f above (409 mg, 1.020 mmol), NMM (0.4 mL, 3.58 mmol) and HOBt (234 mg, 1.734 mmol) in DMF (10 mL) at −15° C. was added EDCI (214 mg, 1.123 mmol). After the reaction was stirred for 30 minutes, it was allowed to warm to room temperature, BnONH2HCl (179 mg, 1.123 mmol) was then added and the reaction was stirred overnight. The solvent was removed under vacuum; the residue was diluted with EtOAc and washed with brine. The combined organic layers were dried and concentrated; the crude product was purified by silica gel column chromatography which gave the title compound as an oil (426 mg, 83% yield).

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe solvent was removed under vacuum
  3. additionthe residue was diluted with EtOAc
  4. washwashed with brine
  5. customThe combined organic layers were dried
  6. concentrationconcentrated
  7. customthe crude product was purified by silica gel column chromatography which

Sources & evidence

ORD record
ord-a7bbe95e7c184adbb2a5b182f854c69e
Source dataset
uspto-grants-2011_09
Patent number
US08022092B2

Reaction notes

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