4-Methylmorpholine → 4-Bromo-1-[4-(3-chloro-4-fluoro-phenylamino)-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl]-but-2-en-1-one
Reaction equation
[Br:1][CH2:2]/[CH:3]=[CH:4]/[C:5]([OH:7])=O.ClC(OCC(C)C)=O.CN1CCOCC1.[Cl:23][C:24]1[CH:25]=[C:26]([NH:31][C:32]2[C:44]3[C:43]4[CH2:42][CH2:41][NH:40][CH2:39][C:38]=4[S:37][C:36]=3[N:35]=[CH:34][N:33]=2)[CH:27]=[CH:28][C:29]=1[F:30]>ClCCl.CO.C(Cl)Cl>[Br:1][CH2:2][CH:3]=[CH:4][C:5]([N:40]1[CH2:39][C:38]2[S:37][C:36]3[N:35]=[CH:34][N:33]=[C:32]([NH:31][C:26]4[CH:27]=[CH:28][C:29]([F:30])=[C:24]([Cl:23])[CH:25]=4)[C:44]=3[C:43]=2[CH2:42][CH2:41]1)=[O:7]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-Bromo crotonic acid (2.07 g, 0.012 mol) in dichloromethane (48 ml) at 0-5° C. was added isobutyl chloroformate (1.70 ml, 0.013 mol) followed by 4-methylmorpholine (1.40 ml, 0.013 mol) under nitrogen. This mixture was stirred at this temp. for one hour. The resulting suspension was added to a cooled solution of (3-Chloro-4-fluoro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine (4.0 g, 0.012 mol) in dichloromethane (200 ml) over a period of 10 min. This mixture was stirred at RT for 1.5 hours. TLC (10% MeOH/DCM) shows no starting material present. The mixture was used as such in further reaction. LCMS RT=3.55 min, [M+H]+=483.04.
Workup
- stirringThis mixture was stirred at RT for 1.5 hours
- customsuch in further reaction
Sources & evidence
- ORD record
- ord-5caf8cc66e344645a8740ebd21bfc634
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501755B2
Reaction notes
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