Sulfanilamide → HCID 25132458, compound

HRID 535930Notes

Reaction equation

HRID 535930 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH2:13][CH2:14][N:15]([CH3:17])[CH2:16][C:11]3=[C:10]([C:18]([OH:20])=O)[N:9]=2)=[C:4]([F:21])[CH:3]=1.CCN(C(C)C)C(C)C.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH2:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH2:13][CH2:14][N:15]([CH3:17])[CH2:16][C:11]3=[C:10]([C:18]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([S:38](=[O:40])(=[O:39])[NH2:41])=[CH:34][CH:33]=3)=[O:20])[N:9]=2)=[C:4]([F:21])[CH:3]=1

Participants

6

Reactant 4

HCID 5333SulfanilamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57635191HCID 57635191, compound

Product 1

HCID 25132458HCID 25132458, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The carboxylic acid intermediate 18D (400 mg) and DIEA (600 μL) were dissolved in DMF (10 mL). An aliquot of this stock solution (400 μL) was dispensed into a vial charged with 4-aminobenzene-sulfonamide (0.10 mmol). TBTU was added (0.50 mmol) to the vial and the mixture was stirred at room temperature for 2 hours. The crude mixture was purified by prep LC-MS using a gradient elution of 5% to 95% MeCN/water in 15 min. The product was taken up with DCM and diluted with hexanes. Evaporation under nitrogen flow gave the desired product, Compound 208 as a solid. LCMS (+ESI) m/z 464 [M+H]+.

Workup

  1. customThe crude mixture was purified by prep LC-MS
  2. washa gradient elution of 5% to 95% MeCN/water in 15 min
  3. additiondiluted with hexanes
  4. customEvaporation under nitrogen flow

Sources & evidence

ORD record
ord-374943debe0c4a1fa9b1242a01d65bed
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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