4-Methylmorpholine → HCID 69797949, compound

HRID 2180227Notes

Reaction equation

HRID 2180227 reaction equation
C(OC([NH:8][C@H:9]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:10]([OH:14])[C:11]([OH:13])=O)=O)(C)(C)C.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.C(N=C=NC(C)C)(C)C.Cl.Cl.[CH2:51]([NH:58][NH2:59])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>CN(C)C(=O)C.ClCCl>[NH2:8][C@H:9]([CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[CH:10]([OH:14])[C:11]([NH:59][NH:58][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:13]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 12734DiisopropylcarbodiimideHCID 146540Benzylhydrazine dihydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69588616HCID 69588616, compound

Product 1

HCID 69797949HCID 69797949, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of Example 1C (50 mg, 0.17 mmol), 1-hydroxybenzotriazole hydrate (30 mg, 0.22 mmol), and N-methylmorpholine (0.07 mL, 0.63 mmol) in 5:1/dichloromethane:N,N-dimethylacetamide (2 mL) at 0° C. was treated with 1,3-diisopropylcarbodiimide (0.03 mL, 0.21 mmol), and stirred for 5 minutes. The solution was treated with 1-benzylhydrazine dihydrochloride (0.05 g, 0.25 mmol), stirred for 2 hours, and warmed to room temperature over 44 hours. The reaction was washed with 2N HCl and saturated NaHCO3, and concentrated. The concentrate was purified by silica gel chromatography with 3:1/hexanes:ethyl acetate then 1:1/hexanes:ethyl acetate, then dissolved in 4N HCl in dioxane (1 mL), stirred for 1 hour, and concentrated, then purified by HPLC to provide the desired product.

Workup

  1. stirringstirred for 2 hours
  2. washThe reaction was washed with 2N HCl and saturated NaHCO3
  3. concentrationconcentrated
  4. customThe concentrate was purified by silica gel chromatography with 3:1/hexanes
  5. dissolutionethyl acetate then 1:1/hexanes:ethyl acetate, then dissolved in 4N HCl in dioxane (1 mL)
  6. stirringstirred for 1 hour
  7. concentrationconcentrated
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-14a5470ede1442d69825736e910d59df
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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