Morpholine → [4-[6-Amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-2-methyl-phenyl]-morpholino-methanone
Reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:34][C:35]1[N:40]=[CH:39][C:38]([C:41]2[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[C:43]([CH3:50])[CH:42]=2)=[CH:37][C:36]=1[C:51]1[N:52]=[N:53][N:54]([CH:56]([CH3:58])[CH3:57])[CH:55]=1.[NH:59]1[CH2:64][CH2:63][O:62][CH2:61][CH2:60]1>CN(C=O)C>[NH2:34][C:35]1[N:40]=[CH:39][C:38]([C:41]2[CH:49]=[CH:48][C:44]([C:45]([N:59]3[CH2:64][CH2:63][O:62][CH2:61][CH2:60]3)=[O:46])=[C:43]([CH3:50])[CH:42]=2)=[CH:37][C:36]=1[C:51]1[N:52]=[N:53][N:54]([CH:56]([CH3:58])[CH3:57])[CH:55]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
HATU (336 mg, 0.88 mmol) and DIPEA (0.30 mL, 1.77 mmol) were added to a solution of 4-(6-amino-5-(1-isopropyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-2-methylbenzoic acid (200 mg, 0.59 mmol) in DMF (10.0 mL) at room temperature, after 5 min, morpholine (0.06 mL, 0.71 mmol) was added, stirred at RT for 18 h. The reaction mixture was poured into ice cold water, extracted with EtOAc (2×50 mL). The organic layer was washed with brine solution (20 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure. Crude product was purified by washing with ether to afford 148 mg of (Yield: 61.4%) of the title compound as a white solid.
Workup
- additionThe reaction mixture was poured into ice cold water
- extractionextracted with EtOAc (2×50 mL)
- washThe organic layer was washed with brine solution (20 mL)
- dry with materialdried over anhydrous Na2SO4 and solvent
- customwas evaporated under reduced pressure
- customCrude product was purified
- washby washing with ether
Sources & evidence
- ORD record
- ord-3cf4398ac27043bfa8a8462522056f60
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321748B2
Reaction notes
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