Di-tert-butyl dicarbonate → N-{4-[3-(4-tert-Butylbenzyl)ureidomethyl]-2-trifluoromethyl-6-vinylphenyl}methanesulfonamide
Reaction equation
C(C1C=CC(CN)=CC=1)(C)(C)C.O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.[C:28]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][N:39]=[C:40]=[O:41])=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29].[NH2:42][CH2:43][C:44]1[CH:49]=[C:48]([CH:50]=[CH2:51])[C:47]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])=[C:46]([C:57]([F:60])([F:59])[F:58])[CH:45]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:28]([C:32]1[CH:33]=[CH:34][C:35]([CH2:38][NH:39][C:40](=[O:41])[NH:42][CH2:43][C:44]2[CH:49]=[C:48]([CH:50]=[CH2:51])[C:47]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])=[C:46]([C:57]([F:60])([F:58])[F:59])[CH:45]=2)=[CH:36][CH:37]=1)([CH3:31])([CH3:29])[CH3:30]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
4-tert-Butyl-benzylamine (1.5 eq, 15.20 μl, 0.09 mmol), BOC2O (1.5 eq, 0.09 mmol, 20.70 μl), and DMAP (0.2 eq, 0.01 mmol, 1.34 mg) were added to methylene chloride. The reaction mixture was stirred for 5 hr. After confirming the synthesis of the 1-tert-butyl-4-isocyanatomethylbenzene with TLC, N-(4-Aminomethyl-2-trifluoromethyl-6-vinylphenyl)methanesulfonamide (1 eq, 0.06 mmol, 20.5 mg) and TEA (2 eq, 0.12 mmol, 16.72 μl) were added into the reaction mixture. The reaction mixture was stirred for 12 hr and purified with similar procedure to step 7 of example 8 to gave title compound (10.7 mg 36.88%).
Workup
- additionwere added into the reaction mixture
- stirringThe reaction mixture was stirred for 12 hr
- custompurified with similar procedure to step 7 of example 8
Sources & evidence
- ORD record
- ord-8c561c387b4e4d29a01cdb79b87c7353
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763657B2
Reaction notes
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