4-Methylmorpholine → HCID 86706384, compound

HRID 1396950Notes

Reaction equation

HRID 1396950 reaction equation
[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:14]([N:16]1[C@H:20]([C:21](O)=[O:22])[CH2:19][CH:18]=[N:17]1)=[O:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2].[F:29][C:30]1[CH:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=1.CN1CCOCC1.ClC1N=C(OC)N=C(OC)N=1>C(#N)C>[F:29][C:30]1[CH:31]=[CH:32][C:33]([NH:36][C:21]([C@H:20]2[N:16]([C:14](=[O:15])[C@@H:13]([CH2:12][N:3]([CH:1]=[O:2])[O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:17]=[CH:18][CH2:19]2)=[O:22])=[N:34][CH:35]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 27377012-Amino-5-fluoropyridineHCID 86706385HCID 86706385, compound

Product 1

HCID 86706384HCID 86706384, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (5S)-1-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid (100 mg, 0.26 mmol) and 5-fluoro-2-pyridinamine (37 mg, 0.33 mmol) in acetonitrile (10 mL) was added 4-methylmorpholine (39 mg, 0.39 mmol) and 2-chloro-4,6-bis(methyloxy)-1,3,5-triazine (49.5 mg, 0.28 mmol). The mixture was stirred at rt overnight. LCMS showed that the reaction was complete. The solvent was removed under vacuum and ethyl acetate was added. The mixture was washed with 10% KHSO4, sat. NaHCO3, brine, dried and concentrated. The residue was purified by flash column chromatography eluting with petroleum ether/ethyl acetate (3:1 to 1:1) to provide the titled compound (108 mg, 85%) as a yellow oil.

Workup

  1. customThe solvent was removed under vacuum and ethyl acetate
  2. additionwas added
  3. washThe mixture was washed with 10% KHSO4, sat. NaHCO3, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. washeluting with petroleum ether/ethyl acetate (3:1 to 1:1)

Sources & evidence

ORD record
ord-08619f1420664f0c9ec8887cce21a5e4
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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