Triethylamine → Spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-yl(4-(2,2,2-trifluoroethoxy)phenyl)methanone
Reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:40]1[CH2:45][CH2:44][C:43]2([O:50][C:49]3[CH:51]=[CH:52][CH:53]=[CH:54][C:48]=3[N:47]3[CH:55]=[CH:56][CH:57]=[C:46]23)[CH2:42][CH2:41]1.CCN(CC)CC>CN(C=O)C>[N:40]1([C:9]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:1])([F:15])[F:14])=[CH:13][CH:12]=2)=[O:11])[CH2:41][CH2:42][C:43]2([O:50][C:49]3[CH:51]=[CH:52][CH:53]=[CH:54][C:48]=3[N:47]3[CH:55]=[CH:56][CH:57]=[C:46]23)[CH2:44][CH2:45]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(2,2,2-Trifluoroethoxy)benzoic acid (22 mg, 0.10 mmol), HATU (42 mg, 0.11 mmol), and DMF (0.8 mL) were combined and allowed to stir at room temperature for 10 minutes. The activated acid was then added to spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine] (28 mg, 0.10 mmol) followed by the addition of Et3N (84 μL, 0.60 mmol). The reaction mixture was stirred at room temperature for 17 h before it was filtered and purified by prep-HPLC (5 mM HCl/H2O and MeOH) to provide spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl(4-(2,2,2-trifluoroethoxy)phenyl)methanone. ESI-MS m/z calc. 442.2, found 443.4 (M+1)+. Retention time: 2.05 minutes (4 min run).
Workup
- stirringThe reaction mixture was stirred at room temperature for 17 h before it
- filtrationwas filtered
- custompurified by prep-HPLC (5 mM HCl/H2O and MeOH)
Sources & evidence
- ORD record
- ord-701fa22ada574f5a92d4e26ff50a7b11
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365588B2
Reaction notes
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