1,2-Dichloroethane → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide
Reaction equation
[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4[O:18][C:19]5[CH:25]=[CH:24][C:23]([C:26]([OH:28])=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.C([NH2:37])C1OC=CC=1.[CH2:38](Cl)[CH2:39]Cl.C1C=CC2N(O)N=NC=2C=1.C[CH2:53][N:54]([CH:58](C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[CH3:53][N:54]([CH3:58])[C:26]([C:23]1[CH:24]=[CH:25][C:19]2[O:18][C:17]([CH2:16][O:15][C:14]3[CH:29]=[CH:30][C:11]([C:1]45[CH2:8][CH:7]6[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]6)[CH2:10]4)[CH2:2]5)=[CH:12][CH:13]=3)=[N:37][C:38]=2[CH:39]=1)=[O:28]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (30.1 mg, 0.08 mmol), furfuryl amine (11.0 mg, 0.12 mmol, 0.01 ml), EDC (21.7 mg, 0.12 mmol) and HOBt (15.4 mg, 0.12 mmol) in DMF 3.0 mL was added DIPEA (14.2 mg, 0.12 mmol, 0.02 ml). After string at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (n-Hexane:EtOAc:MeOH=6:3:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide as a white solid (32.9 mg, 90.9% yield).
Workup
- customAfter string at room temperature, the mixture was partitioned between ethyl acetate and brine
- dry with materialThe organic phase was dried (MgSO4 anh)
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (n-Hexane:EtOAc:MeOH=6:3:1)
Sources & evidence
- ORD record
- ord-7ab7cd6ccbd24ca99f72be340fac1f4f
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394799B2
Reaction notes
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