1,2-Dichloroethane → HCID 57722415, compound

HRID 1986649Notes

Reaction equation

HRID 1986649 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[C:16]3[S:17][C:18]([C:20]([OH:22])=O)=[CH:19][C:15]=3[CH:14]=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:37][C:38]1[C:39]([O:53][CH3:54])=[C:40]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])[CH:41]=[C:42]([C:44]([CH3:47])([CH3:46])[CH3:45])[CH:43]=1>CN(C=O)C>[C:44]([C:42]1[CH:41]=[C:40]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])[C:39]([O:53][CH3:54])=[C:38]([NH:37][C:20]([C:18]2[S:17][C:16]3[C:11]([NH:10][C:8](=[O:9])[C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=4)=[CH:12][CH:13]=[CH:14][C:15]=3[CH:19]=2)=[O:22])[CH:43]=1)([CH3:47])([CH3:45])[CH3:46]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 57722438HCID 57722438, compound

Product 1

HCID 57722415HCID 57722415, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the above carboxylic acid (50 mg) in DMF (1.5 mL) was added EDC (1.5 eq) and HOBT (1.5 eq). The reaction was stirred at room temperature for 15 min, then N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (1.2 eq) was added. The reaction was stirred 12 h, then the DMF was removed in vacuo, the residue was taken up in EtOAc and washed with water, followed by brine. The organics were dried over MgSO4, filtered, and concentrated and the residue was purified by flash chromatography on silica gel (20%-60% EtOAc/hexane) to give the title compound as a white solid (36 mg, 41% yield for two steps).

Workup

  1. stirringThe reaction was stirred 12 h
  2. customthe DMF was removed in vacuo
  3. washwashed with water
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by flash chromatography on silica gel (20%-60% EtOAc/hexane)

Sources & evidence

ORD record
ord-f96e3975a9c24f5a8d7087dc9f488078
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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