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1,2-Dichloroethane → HCID 57722415, compound

HRID 1986664
Notes
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Reaction equation

HRID 1986664 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-72a26d01b8234ce1b5f05bb8087dad27
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07550461B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes