Morpholine → HCID 66558139, compound

HRID 41224Notes

Reaction equation

HRID 41224 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]1[CH:25]=[C:26]([N:30]2[CH2:34][CH2:33][CH2:32][CH:31]2[C:35]2[CH:36]=[C:37]([C:53]([OH:55])=O)[CH:38]=[C:39]3[C:44]=2[O:43][C:42]([N:45]2[CH2:50][CH2:49][O:48][C@H:47]([CH3:51])[CH2:46]2)=[CH:41][C:40]3=[O:52])[CH:27]=[CH:28][CH:29]=1.CCN(C(C)C)C(C)C.[NH:65]1[CH2:70][CH2:69][O:68][CH2:67][CH2:66]1>CN(C=O)C>[F:23][C:24]1[CH:25]=[C:26]([N:30]2[CH2:34][CH2:33][CH2:32][CH:31]2[C:35]2[CH:36]=[C:37]([C:53]([N:65]3[CH2:70][CH2:69][O:68][CH2:67][CH2:66]3)=[O:55])[CH:38]=[C:39]3[C:44]=2[O:43][C:42]([N:45]2[CH2:50][CH2:49][O:48][C@H:47]([CH3:51])[CH2:46]2)=[CH:41][C:40]3=[O:52])[CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866724438-(1-(3-fluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid

Product 1

HCID 66558139HCID 66558139, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TBTU (138 mg, 0.43 mmol) was added to a stirred solution of 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid (97 mg, 0.21 mmol), DIPEA (0.075 mL, 0.43 mmol) dissolved in DMF (1.5 mL) under nitrogen. The resulting solution was stirred at room temperature for 1.5 h. Morpholine (0.028 mL, 0.32 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was purified by preparative HPLC. The fractions were evaporated to dryness, the residue was dissolved in DCM, dried over MgSO4 and evaporated to dryness to afford 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-6-(morpholine-4-carbonyl)-4H-chromen-4-one (63 mg, 56%) as a yellow foam.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 1 h
  2. customThe reaction mixture was purified by preparative HPLC
  3. customThe fractions were evaporated to dryness
  4. dissolutionthe residue was dissolved in DCM
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-6ed6ebc005e147c1bfcf9aaf1bdf3635
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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