1,2-Dichloroethane → HCID 25175792, compound

HRID 2190345Notes

Reaction equation

HRID 2190345 reaction equation
C1C=[C:5]2[N:7]=NN(O)C2=CC=1.O.C(Cl)CCl.[Cl:16][C:17]1[S:21][C:20]([NH:22][C:23](=[O:49])[N:24]([C:40]2[CH:41]=[C:42]([CH:46]=[CH:47][CH:48]=2)[C:43]([OH:45])=O)[CH2:25][CH2:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:19][C:18]=1[C:50]1[CH:55]=[CH:54][C:53]([NH:56][S:57]([CH3:60])(=[O:59])=[O:58])=[CH:52][CH:51]=1.CN>CCOC(C)=O.CN(C=O)C>[Cl:16][C:17]1[S:21][C:20]([NH:22][C:23]([N:24]([CH2:25][CH2:26][CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]2[CH:41]=[C:42]([CH:46]=[CH:47][CH:48]=2)[C:43]([NH:7][CH3:5])=[O:45])=[O:49])=[N:19][C:18]=1[C:50]1[CH:51]=[CH:52][C:53]([NH:56][S:57]([CH3:60])(=[O:59])=[O:58])=[CH:54][CH:55]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 25175638HCID 25175638, compound

Product 1

HCID 25175792HCID 25175792, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of HOBt hydrate (0.042 g, 0.27 mmol), EDC (0.037 g, 0.19 mmol), and 3-(3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)benzoic acid 78 (0.089 g, 0.13 mmol) was added DMF (1.5 mL). The reaction mixture was stirred at room temperature for 10 min and methylamine (2 mL, 2 M in MeOH, 4 mmol) was added. The reaction mixture was stirred at room temperature for 1 d and diluted with EtOAc. The organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 20% to 80% EtOAc in hexanes) gave 3-(((5-chloro-4-(4-((methylsulfonyl)amino)phenyl)-1,3-thiazol-2-yl)carbamoyl)(3,3-diphenylpropyl)amino)-N-methylbenzamide 79. Mass spectrum, calculated for C34H32ClN5O4S2 673.2; found 674.2 (M++1).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 d
  2. washThe organic phase was washed with water (1×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel (eluted with 20% to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e9eb2a3272144ababe548cd15204e19a
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

Loading…