4-Methylmorpholine → HCID 22475135, compound

HRID 2184151Notes

Reaction equation

HRID 2184151 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=3)[O:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:11]=3[O:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.CN(C(ON1N=[N:44][C:39]2C=[CH:41][CH:42]=[CH:43][C:38]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.N1CCCCC1>C(OCC)(=O)C.CN(C=O)C>[F:28][C:23]1[CH:22]=[C:21]([C:9]2([C:4]3[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=3)[O:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]([N:44]4[CH2:41][CH2:42][CH2:43][CH2:38][CH2:39]4)=[O:20])=[CH:17][C:11]=3[O:10]2)[CH:26]=[C:25]([F:27])[CH:24]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8082PiperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22475247HCID 22475247, compound

Product 1

HCID 22475135HCID 22475135, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

96 mg 2,2-bis-(3,5-difluoro-phenyl)-benzo[1,3]dioxole-5-carboxylic acid, 93 mg HBTU, 1 mL DMF and 50 mg N-methylmorpholine were stirred at room temperature. After 5 min 21 mg piperidine were added and the mixture stirred at room temperature for 24 h. The mixture was diluted with ethyl acetate and washed twice with water. Evaporation of the solvents and purification on silica gel afforded 111 mg of a white foam, MS: 457 ([M]+).

Workup

  1. washwashed twice with water
  2. customEvaporation of the solvents and purification on silica gel

Sources & evidence

ORD record
ord-f789a04dc58c45f3a2513faffb737dec
Source dataset
uspto-grants-2005_05
Patent number
US06900227B2

Reaction notes

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