4-Methylmorpholine → HCID 58505489, compound

HRID 475448Notes

Reaction equation

HRID 475448 reaction equation
[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][NH2:27])[CH:21]=3)=[CH:18][CH:19]=2)=[O:14])[C:8](=[O:11])[NH:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.Cl[C:36]([O:38][CH2:39][CH:40]([CH3:42])[CH3:41])=[O:37]>CN(C=O)C>[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=3)[CH2:26][NH:27][C:36](=[O:37])[O:38][CH2:39][CH:40]([CH3:42])[CH3:41])=[CH:18][CH:19]=2)=[O:14])[C:8]([NH:9][CH3:10])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 58505441HCID 58505441, compound

Product 1

HCID 58505489HCID 58505489, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(3-aminomethyl-phenyl)-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (37 mg, 0.10 mmol) in DMF (2.0 mL) is added 4-methylmorpholine (44 μL, 0.40 mmol) followed by isobutyl chloroformate (21 mg, 0.15 mmol). After stirring at room temperature for 12 hours, the mixture is evaporated in vacuo and the resulting oil purified on reverse phase HPLC to obtain a white solid, 26 mg, 54%, LC/MS ESI m/z (M+H)+=470.4.

Workup

  1. customthe mixture is evaporated in vacuo
  2. customthe resulting oil purified on reverse phase HPLC
  3. customto obtain a white solid, 26 mg, 54%, LC/MS ESI m/z (M+H)+=470.4

Sources & evidence

ORD record
ord-ae920df834884b7eba50832c5108b207
Source dataset
uspto-grants-2014_01
Patent number
US08637550B2

Reaction notes

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