Morpholine → HCID 67147485, compound

HRID 490430Notes

Reaction equation

HRID 490430 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][C:35]=1[O:36][CH3:37])[N:32]([CH2:38][CH2:39][C:40]([OH:42])=O)[CH:31]=[C:30]2[C:43]1[NH:51][C:46]2=[N:47][CH:48]=[CH:49][CH:50]=[C:45]2[CH:44]=1.[NH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C.O>[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][C:35]=1[O:36][CH3:37])[N:32]([CH2:38][CH2:39][C:40]([N:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1)=[O:42])[CH:31]=[C:30]2[C:43]1[NH:51][C:46]2=[N:47][CH:48]=[CH:49][CH:50]=[C:45]2[CH:44]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67147433HCID 67147433, compound

Product 1

HCID 67147485HCID 67147485, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.036 g of O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate is added to a solution of 0.035 g of 3-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]propionic acid in 3 ml of dimethylformamide, under an inert argon atmosphere at a temperature in the region of 20° C. The reaction medium is agitated at this temperature for 1 hour. 0.01 ml of morpholine and then 0.017 ml of diisopropylethylamine are added. After agitation at the same temperature for 3 hours, 10 ml of water and 10 ml of ethyl acetate are added. After separation by settling out, the organic phase is dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents). The fractions containing the product are concentrated under reduced pressure. 0.025 g of 3-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]-1-morpholin-4-ylpropan-1-one is thus obtained, the characteristics of which are as follows:

Workup

  1. waitAfter agitation at the same temperature for 3 hours
  2. customAfter separation
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by flash-pack chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents)
  8. additionThe fractions containing the product
  9. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-af6381b9e4984ffeac980d1251c54130
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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