4-Methylmorpholine → HCID 86603133, compound

HRID 855453Notes

Reaction equation

HRID 855453 reaction equation
CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:32][C:33]1[CH:34]=[C:35]2[C:39](=[C:40]([C:42]([OH:44])=O)[CH:41]=1)[NH:38][CH:37]=[CH:36]2.[F:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][CH2:53][NH:54][CH2:55][C:56]2[CH:61]=[CH:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][CH:57]=2)=[CH:48][CH:47]=1>CN(C=O)C.O>[F:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][CH2:53][N:54]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([C:62]([F:63])([F:64])[F:65])=[CH:58][CH:57]=2)[C:42]([C:40]2[CH:41]=[C:33]([Cl:32])[CH:34]=[C:35]3[C:39]=2[NH:38][CH:37]=[CH:36]3)=[O:44])=[CH:48][CH:47]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 29558679HCID 29558679, compoundHCID 668685635-chloro-1H-indole-7-carboxylic acid

Product 1

HCID 86603133HCID 86603133, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

121 mg (1.2 mmol) of N-methyl morpholine and then 227 mg (0.6 mmol) of HBTU were added to 78 mg (0.40 mmol) of 5-chloro-1H-indol-7-carboxylic acid and 142 mg (0.48 mmol) of [2-(4-fluoro-phenyl)-ethyl]-(4-trifluoromethyl-benzyl)-amine dissolved in 4 ml DMF at rt under nitrogen. The reaction mixture was stirred at rt over night. Water was added and the reaction mixture was extracted twice with EtOAc. The combined organic layers were washed once with 1N aqueous HCl solution, once with saturated aqueous NaHCO3 solution and once with saturated aqueous NaCl. Solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (20 g silica gel; heptane/EtOAc 7:3) to yield 178 mg (94%) product as a yellow viscous oil. MS (ISP) 475.1 (M+H)+.

Workup

  1. extractionthe reaction mixture was extracted twice with EtOAc
  2. washThe combined organic layers were washed once with 1N aqueous HCl solution, once with saturated aqueous NaHCO3 solution and once with saturated aqueous NaCl
  3. dry with materialSolution, dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (20 g silica gel; heptane/EtOAc 7:3)

Sources & evidence

ORD record
ord-fe34e384871c43a4bebcfd145f5ad9ff
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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