Morpholine → HCID 60164657, compound

HRID 513705Notes

Reaction equation

HRID 513705 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]1[CH:32]=[CH:31][C:30]([CH:33]2[C:46]3[CH:45]=[CH:44][C:43]4[C:38](=[N:39][CH:40]=[CH:41][CH:42]=4)[C:37]=3[NH:36][S:35](=[O:48])(=[O:47])[N:34]2[CH3:49])=[CH:29][C:25]=1[C:26]([OH:28])=O.[NH:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[F:23][C:24]1[CH:32]=[CH:31][C:30]([CH:33]2[C:46]3[CH:45]=[CH:44][C:43]4[C:38](=[N:39][CH:40]=[CH:41][CH:42]=4)[C:37]=3[NH:36][S:35](=[O:47])(=[O:48])[N:34]2[CH3:49])=[CH:29][C:25]=1[C:26]([N:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1)=[O:28]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68183192HCID 68183192, compound

Product 1

HCID 60164657HCID 60164657, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

TBTU (49.73 mg, 0.15 mmol) was added to a suspension of 2-fluoro-5-(2-methyl-3,3-dioxo-1,2,3,4-tetrahydro-3λ*6*-thia-2,4,5-triaza-phenanthren-1-yl)-benzoic acid 424 (60 mg, 0.15 mmol) in DCM (1 ml) and the mixture was stirred at room temperature for 20 min. Morpholine (13.6 μl, 0.15 mmol) and DIPEA (25.6 μl, 0.15 mmol) were added and the mixture was stirred at room temperature for 3 h. The mixture was diluted with water (1 ml) and the mixture was extracted with DCM (3 ml). The organic phase was concentrated in vacuo. The crude residue was purified by preparative HPLC (acidic conditions 1) to give the title compound (32 mg, 45%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 h
  2. extractionthe mixture was extracted with DCM (3 ml)
  3. concentrationThe organic phase was concentrated in vacuo
  4. customThe crude residue was purified by preparative HPLC (acidic conditions 1)

Sources & evidence

ORD record
ord-ef07806ca43f4e3fb423a6f1ee904027
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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