Dimethylformamide → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-dimethylamino-ethyl)-amide
Reaction equation
[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4[O:18]C5C=CC(C(O)=O)=CC=5N=4)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.N1(CCCN)CCOCC1.CN(C(ON1N=[N:56][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[CH2:66][N:67]([CH:71](C)C)[CH:68]([CH3:70])C.C[N:75]([CH:77]=[O:78])C>>[CH3:71][N:67]([CH3:66])[CH2:68][CH2:70][NH:75][C:77]([C:53]1[CH:54]=[CH:55][C:50]2[O:18][C:17]([CH2:16][O:15][C:14]3[CH:13]=[CH:12][C:11]([C:1]45[CH2:10][CH:5]6[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]6)[CH2:2]4)[CH2:8]5)=[CH:30][CH:29]=3)=[N:56][C:51]=2[CH:52]=1)=[O:78]Participants
6
Reactant 5
Product 1
Procedure
To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (57.7 mg, 0.14 mmol) and 3-morpholine-4-yl-propylamine (0.031 ml, 0.29 mmol) in DMF 4.0 mL was added HBTU (109.98 mg, 0.29 mmol) and DIPEA (0.051 ml, 0.29 mmol). After stilling at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrate. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=10:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-dimethylamino-ethyl)-amide as a white solid (38.2 mg, 58% yield).
Workup
- customAfter stilling at room temperature
- customthe mixture was partitioned between ethyl acetate and brine
- dry with materialThe organic phase was dried (MgSO4 anh)
- concentrationconcentrate
- customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=10:1)
Sources & evidence
- ORD record
- ord-898e7d416fc441328c8597a380d352bd
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394799B2
Reaction notes
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