Morpholine → 2-((R)-2-methylmorpholino)-6-(morpholine-4-carbonyl)-8-(1-phenylpyrrolidin-2-yl)-4H-chromen-4-one

HRID 41222Notes

Reaction equation

HRID 41222 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:23][C@@H:24]1[CH2:29][N:28]([C:30]2[O:31][C:32]3[C:37]([C:38](=[O:40])[CH:39]=2)=[CH:36][C:35]([C:41]([OH:43])=O)=[CH:34][C:33]=3[CH:44]2[CH2:48][CH2:47][CH2:46][N:45]2[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:27][CH2:26][O:25]1.CCN(C(C)C)C(C)C.[NH:64]1[CH2:69][CH2:68][O:67][CH2:66][CH2:65]1>CC(N(C)C)=O>[CH3:23][C@@H:24]1[CH2:29][N:28]([C:30]2[O:31][C:32]3[C:37]([C:38](=[O:40])[CH:39]=2)=[CH:36][C:35]([C:41]([N:64]2[CH2:69][CH2:68][O:67][CH2:66][CH2:65]2)=[O:43])=[CH:34][C:33]=3[CH:44]2[CH2:48][CH2:47][CH2:46][N:45]2[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH2:27][CH2:26][O:25]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86672441HCID 86672441, compound

Product 1

HCID 866724402-((R)-2-methylmorpholino)-6-(morpholine-4-carbonyl)-8-(1-phenylpyrrolidin-2-yl)-4H-chromen-4-oneYield 66.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

TBTU (148 mg, 0.46 mmol) was added to a stirred solution of 2-((R)-2-methylmorpholino)-4-oxo-8-(1-phenylpyrrolidin-2-yl)-4H-chromene-6-carboxylic acid (80 mg, 0.18 mmol), DIPEA (0.080 mL, 0.46 mmol) dissolved in DMA (2 mL) under nitrogen. The resulting solution was stirred at room temperature for 30 min. Morpholine (0.048 mL, 0.55 mmol) was added to the mixture and stirred at room temperature for 1 h. The reaction mixture was purified by preparative HPLC. The fractions containing the desired compound were evaporated to dryness to afford 2-((R)-2-methylmorpholino)-6-(morpholine-4-carbonyl)-8-(1-phenylpyrrolidin-2-yl)-4H-chromen-4-one (60 mg, 65%) as a gummy solid.

Workup

  1. stirringstirred at room temperature for 1 h
  2. customThe reaction mixture was purified by preparative HPLC
  3. additionThe fractions containing the desired compound
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-1d1d702488c84784ab1124a879cffa71
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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