Chlorosuccinimide → Tert-butyl 4-(2-(3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)ethyl)piperidine-1-carboxylate

HRID 2190335Notes

Reaction equation

HRID 2190335 reaction equation
[C:1]1([CH:7]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:8][CH2:9][N:10]([CH2:30][CH2:31][CH:32]2[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]2)[C:11]([NH:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)[N:18]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Cl:58])C(=O)C1>CN(C=O)C>[Cl:58][C:16]1[S:15][C:14]([NH:13][C:11](=[O:12])[N:10]([CH2:30][CH2:31][CH:32]2[CH2:33][CH2:34][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:42])[CH3:43])=[O:39])[CH2:36][CH2:37]2)[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[N:18][C:17]=1[C:19]1[CH:20]=[CH:21][C:22]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57586428Tert-butyl 4-(2-(1-(3,3-diphenylpropyl)-3-(4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)ureido)ethyl)piperidine-1-carboxylate

Product 1

HCID 57586321Tert-butyl 4-(2-(3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To tert-butyl 4-(2-(1-(3,3-diphenylpropyl)-3-(4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)ureido)ethyl)piperidine-1-carboxylate (0.35 g, 0.49 mmol) in DMF (10 ml) was added NCS (0.065 g, 0.49 mmol). The resulting mixture was stirred overnight at room temperature. After this time the mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and sat. aq. NaHCO3. The organic layer was washed with water and brine, dried over MgSO4 and concentrated under reduced pressure to give the crude product as a thick yellow oil. This crude product was purified by combi-flash (10-50% EtOAc/hexane). To give tert-butyl 4-(2-(3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)ethyl)piperidine-1-carboxylate 50 as a yellow oil.

Workup

  1. concentrationAfter this time the mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and sat. aq. NaHCO3
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product as a thick yellow oil
  7. customThis crude product was purified by combi-flash (10-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-8e43b12dcfd64b0f9882efa3a484d517
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

Loading…