4-Methylmorpholine → HCID 10050252, compound

HRID 2375434Notes

Reaction equation

HRID 2375434 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4](=[O:12])[N:3]=1.[C:13]([C:15]1([NH:24][C:25](=[O:35])[CH:26]([NH2:34])[CH2:27][CH2:28][C:29]([CH3:33])([CH3:32])[CH2:30][CH3:31])[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH3:23])[CH2:17][CH2:16]1)#[N:14].CN1CCOCC1>C(#N)C>[C:13]([C:15]1([NH:24][C:25](=[O:35])[CH:26]([NH:34][C:2]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[O:5][C:4](=[O:12])[N:3]=2)[CH2:27][CH2:28][C:29]([CH3:33])([CH3:32])[CH2:30][CH3:31])[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH3:23])[CH2:19][CH2:20]1)#[N:14]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 113098874-Chloro-benzo[e][1,3]oxazin-2-oneHCID 59654225HCID 59654225, compound

Product 1

HCID 10050252HCID 10050252, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-chloro-benzo[e][1,3]oxazin-2-one (620 mg, 3.41 mmol, 2.0 eq), 2-amino-5,5-dimethyl-heptanoic acid (4-cyano-1-propyl-piperidin-4-yl)-amide (675 mg, 1.71 mmol, 1.00 eq), and 4-methylmorpholine (NMM) (0.56 mL, 5.09 mmol, 3.00 eq) in acetonitrile (9.0 mL) was stirred at room temperature overnight. The reaction mixture was then concentrated, resuspended in ethyl acetate (50 mL) and washed with saturated Na2CO3 solution. The organic phase was dried (MgSO4) and concentrated and the resulting residue was chromatographed over silica gel using a gradient of methanol in dichloromethane as the eluant to provide 124 mg (16% yield) of the title compound; m/z calculated for C26H37N5O3 467.6, found 468.4 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. washwashed with saturated Na2CO3 solution
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customthe resulting residue was chromatographed over silica gel using a gradient of methanol in dichloromethane as the eluant

Sources & evidence

ORD record
ord-a19a870f580449449f848f5eeb3d6bcc
Source dataset
uspto-grants-2008_12
Patent number
US07465745B2

Reaction notes

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