Morpholine → HCID 67394150, compound

HRID 908665Notes

Reaction equation

HRID 908665 reaction equation
F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]2[S:34][C:33]([C:35]([OH:37])=O)=[N:32][C:31]=2[C:38]=1[N+:39]([O-:41])=[O:40].C(N(C(C)C)CC)(C)C.[NH:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1.CN(C1C=CC=CN=1)C>ClCCl.CCCCCCC.C(OCC)(=O)C>[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]2[S:34][C:33]([C:35]([N:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[O:37])=[N:32][C:31]=2[C:38]=1[N+:39]([O-:41])=[O:40]

Participants

9

Reactant 5

HCID 8083MorpholineHCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 454803595-Methoxy-4-nitro-1,3-benzothiazole-2-carboxylic acid

Product 1

HCID 67394150HCID 67394150, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

980 mg (2.1 mmol; 1.1 eq.) of bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBroP) is added to 500 mg (1.97 mmol) of 5-methoxy-4-nitro-1,3-benzothiazole-2-carboxylic acid and 344 μl (1.97 mmol; 1 eq.) of diisopropylethylamine in solution in 40 ml of dichloromethane. The reaction mixture is maintained for 15 minutes under stirring at ambient temperature, then 202 μl (2.3 mmol; 1.2 eq.) of morpholine and a spatula tip's worth of dimethylaminopyridine are added to the medium which is maintained under stirring for 18 hours at ambient temperature. An insoluble part is then filtered and the solvent evaporated off under reduced pressure. The residue is then purified on a silica column (eluent: ethyl acetate/heptane: gradient of 30 to 70% over 40 minutes then for 5 minutes at 70% of ethyl acetate in heptane) and 210 mg (yield=33%) of expected product is obtained in the form of beige powder.

Workup

  1. temperatureThe reaction mixture is maintained for 15 minutes
  2. temperatureis maintained
  3. stirringunder stirring for 18 hours at ambient temperature
  4. filtrationAn insoluble part is then filtered
  5. customthe solvent evaporated off under reduced pressure
  6. customThe residue is then purified on a silica column (eluent

Sources & evidence

ORD record
ord-96f27475666143159fa6838fd23f3ec9
Source dataset
uspto-grants-2011_09
Patent number
US08017637B2

Reaction notes

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