4-Methylmorpholine → HCID 178455801, compound

HRID 2111707Notes

Reaction equation

HRID 2111707 reaction equation
[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C[O:24][C:25]([C@@H:27]1[CH2:29][C@H:28]1[CH2:30][N:31]1[CH2:36][CH2:35][CH:34]([C:37]2[C:41]3[S:42][CH:43]=[CH:44][C:40]=3[O:39][N:38]=2)[CH2:33][CH2:32]1)=O.CN1CCOCC1.[CH2:52]([C@H:54]1[CH2:59][CH2:58][C@H:57]([NH2:60])[CH2:56][CH2:55]1)[CH3:53]>CN(C)C=O>[CH2:52]([C@H:54]1[CH2:59][CH2:58][C@H:57]([NH:60][C:25]([C@@H:27]2[CH2:29][C@H:28]2[CH2:30][N:31]2[CH2:36][CH2:35][CH:34]([C:37]3[C:41]4[S:42][CH:43]=[CH:44][C:40]=4[O:39][N:38]=3)[CH2:33][CH2:32]2)=[O:24])[CH2:56][CH2:55]1)[CH3:53]

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 68457315HCID 68457315, compoundHCID 178455800HCID 178455800, compound

Product 1

HCID 178455801HCID 178455801, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add TOTU (415 mg, 1.06 mmol) to a solution of trans-2-(4-thieno[2,3-d]isoxazol-3-yl-piperidin-1-ylmethyl)-cyclopropanecarboxylic acid methyl ester (Example 22b) (300 mg, 1.0 mmol), in dimethylformamide (approximately 10 mL), and allow the reaction to stir at ambient temperature for 0.5 h. Add N-methylmorpholine (107 mg, 1.26 mmol) and trans-4-ethylcyclohexylamine (254 mg, 2.0 mmol), and stir for 6 h. Add additional equivalents of N-methylmorpholine and TOTU and continue to stir for overnight. I think again I didn't write it down Concentrate the reaction and purify the residue by column chromatography over silica gel (dichloromethane/MeOH, gradient 0→30%) to obtain 270 mg (65%), LC/MS, m/z=416 (M+H)+.

Workup

  1. customthe reaction
  2. stirringto stir for overnight
  3. concentrationdown Concentrate
  4. customthe reaction
  5. custompurify the residue by column chromatography over silica gel (dichloromethane/MeOH, gradient 0→30%)
  6. customto obtain 270 mg (65%), LC/MS, m/z=416 (M+H)+

Sources & evidence

ORD record
ord-0aebea8e3c3b402181dcc5a47bf9b66b
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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