1,2-Dichloroethane → 4-Amino-3-methoxy-N-(oxetan-3-yl)benzamide
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[O:36]1[CH2:39][CH:38]([NH2:40])[CH2:37]1>C(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:40][CH:38]2[CH2:39][O:36][CH2:37]2)=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]Participants
7
Procedure
To a solution of 4-amino-3-methoxybenzoic acid (1 equiv) in DCM (0.11 M) was added HOBT (1.2 equiv), EDC (1.2 equiv) and DIEA (4 equiv). Oxetan-3-amine (1.2 equiv) was added then the reaction mixture was stirred at room temperature overnight. The mixture was extracted with ethyl acetate then the organic layer was dried over sodium sulfate The solids were filtered off, the filtrate was concentrated and the product was purified by silica gel chromatography (5% DCM in MeOH) to afford the title compound (53% yield) as a yellow solid. MS (ESI) m/z 223.1 [M+1]+
Workup
- extractionThe mixture was extracted with ethyl acetate
- dry with materialthe organic layer was dried over sodium sulfate The solids
- filtrationwere filtered off
- concentrationthe filtrate was concentrated
- customthe product was purified by silica gel chromatography (5% DCM in MeOH)
Sources & evidence
- ORD record
- ord-6edbae25c99f4d96b66ff05a82c2f20a
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428509B2
Reaction notes
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