Triethylamine → HCID 58551215, compound
Reaction equation
[CH2:1]([C:3]1[CH:30]=[CH:29][C:6]([C:7]([N:9]2[CH2:14][CH2:13][C:12]3([O:19][C:18]4[CH:20]=[C:21]([CH:24]=O)[CH:22]=[CH:23][C:17]=4[N:16]4[CH:26]=[CH:27][CH:28]=[C:15]34)[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[O:31][CH3:32])[CH3:2].C[CH2:34][N:35](CC)[CH2:36]C>CN(C=O)C>[CH3:34][N:35]([CH2:24][C:21]1[CH:22]=[CH:23][C:17]2[N:16]3[CH:26]=[CH:27][CH:28]=[C:15]3[C:12]3([CH2:13][CH2:14][N:9]([C:7]([C:6]4[CH:29]=[CH:30][C:3]([CH2:1][CH3:2])=[C:4]([O:31][CH3:32])[CH:5]=4)=[O:8])[CH2:10][CH2:11]3)[O:19][C:18]=2[CH:20]=1)[CH3:36]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1′-(4-ethyl-3-methoxybenzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-7-carbaldehyde (88 mg, 0.20 mmol) N,N-dimethylamine hydrochloride (83 mg, 1.0 mmol), Et3N (140 μL, 1.0 mmol) and NaHB(OAc)3 (130 mg, 0.60 mmol) in DMF (1 mL) was stirred at room temperature overnight. The reaction mixture was filtered and purified by reverse phase LC-MS (10-99% CH3CN/H2O) to yield (7-((dimethylamino)methyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-ethyl-3-methoxyphenyl)methanone. ESI-MS m/z calc. 459.6, found 460.5 (M+1)+; Retention time: 1.40 minutes (3 min run).