Di-tert-butyl dicarbonate → N-{4-[3-(4-tert-Butylbenzyl)ureidomethyl]-2-chloro-6-vinylphenyl}Methanesulfonamide

HRID 2358384Notes

Reaction equation

HRID 2358384 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]([Cl:57])[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]([Cl:57])[CH:45]=2)=[CH:36][CH:37]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 90495Di-tert-butyl dicarbonateHCID 27356554-tert-ButylbenzylamineHCID 220422271-Tert-butyl-4-(isocyanatomethyl)benzeneHCID 68457636N-(4-Aminomethyl-2-chloro-6-vinylphenyl)methanesulfonamide

Product 1

HCID 11852484N-{4-[3-(4-tert-Butylbenzyl)ureidomethyl]-2-chloro-6-vinylphenyl}MethanesulfonamideYield 17.66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-tert-butylbenzylamine (1.5 eq, 71.10 μl, 0.44 mmol), BOC2O (1.5 eq, 0.44 mmol, 101.19 μl), and DMAP (0.2 eq, 0.06 mmol, 7.08 mg) were added in 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-chloro-6-vinylphenyl)methanesulfonamide (1 eq, 0.29 mmol, 108.6 mg) and TEA (2 eq, 0.58 mmol, 80.84 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 a title compound (23.0 mg, 17.66%).

Workup

  1. additionwere added into the reaction mixture
  2. stirringThe reaction mixture was stirred for 12 hr
  3. custompurified with similar procedure to step 7 of example 8

Sources & evidence

ORD record
ord-099a8fba80374ebaa30a32eded151db7
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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