Benzenesulfonamide, 3-amino- → HCID 25263017, compound

HRID 1897562Notes

Reaction equation

HRID 1897562 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:17]([O:19]CC)=O)[N:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:49][C:50]1[CH:51]=[C:52]([S:56]([NH2:59])(=[O:58])=[O:57])[CH:53]=[CH:54][CH:55]=1>C1COCC1.O.CN(C=O)C>[C:1]([C:5]1[N:6]=[C:7]([C:17]([NH:49][C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([S:56]([NH2:59])(=[O:57])=[O:58])[CH:51]=2)=[O:19])[N:8]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 7377Benzenesulfonamide, 3-amino-HCID 168937Lithium hydroxide, monohydrateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57659740HCID 57659740, compound

Product 1

HCID 25263017HCID 25263017, compoundYield 11.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl 5-tert-butyl-2-benzyl-2H-1,2,4-triazole-3-carboxylate (0.10 g 0.35 mmol) and LiOH.H2O (29 mg, 0.70 mmol) in THF (1 mL) and H2O (1 mL) was stirred at room temperature 2 h. The solvent was evaporated under vacuum, and to the residue was added DMF (2 mL) and HATU (0.13 g, 0.35 mmol). The reaction was stirred for 3 min, then 3-amino-benzenesulfonamide (60 mg, 0.35 mmol) was added. The reaction was stirred for 3 h, diluted with water, and extracted with EtOAc. The organic extracts were washed with water, dried over Na2SO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (0%-5% MeOH-CH2Cl2) to obtain 5-tert-butyl-2-benzyl-N-(3-(aminosulfonyl)phenyl)-2H-1,2,4-triazole-3-carboxamide (16 mg, 11% yield). LC/MS: m/z 414.3 (M+H)+ at 3.46 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe solvent was evaporated under vacuum
  2. stirringThe reaction was stirred for 3 min
  3. stirringThe reaction was stirred for 3 h
  4. extractionextracted with EtOAc
  5. washThe organic extracts were washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel chromatography (0%-5% MeOH-CH2Cl2)

Sources & evidence

ORD record
ord-5d8f8f3034214b3dbc3015f2aef2a25f
Source dataset
uspto-grants-2013_08
Patent number
US08519137B2

Reaction notes

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