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

HRID 2190334Notes

Reaction equation

HRID 2190334 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[NH2:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=2)[N:18]=1.[C:30]1([CH:36]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:37][CH2:38][NH:39][CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[C:55]1([CH:36]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:37][CH2:38][N:39]([CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]2)[C:6]([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:7])[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 7063853N-[4-(2-amino-4-thiazolyl)phenyl]MethanesulfonamideHCID 57586396Tert-butyl 4-(2-(3,3-diphenylpropylamino)ethyl)piperidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

DMAP (0.17 g, 1 0.4 mmol), CDI (0.23 g, 1.4 mmol) and N-(4-(2-aminothiazol-4-yl)phenyl)-methanesulfonamide (0.25 g, 0.93 mmol) were mixed together in DCM/DMF and then stirred overnight at room temperature. After 24 hrs a precipitate had formed. tert-butyl 4-(2-(3,3-diphenylpropylamino)ethyl)piperidine-1-carboxylate (0.39 g, 0.93 mmol) was then added and the resulting mixture stirred for a further 15 hrs. The crude mixture was concentrated under reduced pressure and the residue purified by combi-flash to give tert-butyl 4-(2-(1-(3,3-diphenylpropyl)-3-(4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)ureido)ethyl)piperidine-1-carboxylate 49 as an oily solid.

Workup

  1. customAfter 24 hrs a precipitate had formed
  2. stirringthe resulting mixture stirred for a further 15 hrs
  3. concentrationThe crude mixture was concentrated under reduced pressure
  4. customthe residue purified by combi-flash

Sources & evidence

ORD record
ord-af96ee9b87874216bf58ce5f0851774e
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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