Sulfanilamide → HCID 67421157, compound

HRID 1509789Notes

Reaction equation

HRID 1509789 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)([CH3:4])([CH3:3])[CH3:2].[S:25]([NH2:35])(=[O:34])([C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1)=[O:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCN(CC)CC>[O:16]=[C:14]([NH:33][C:30]1[CH:31]=[CH:32][C:27]([S:25](=[O:34])(=[O:26])[NH2:35])=[CH:28][CH:29]=1)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:24]

Participants

6

Reactant 3

HCID 5333SulfanilamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57776706HCID 57776706, compound

Product 1

HCID 67421157HCID 67421157, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 6-((2-tert-butoxy-2-oxoethyl)(pyridin-2-ylmethyl)amino)hexanoic acid (0.6545 g, 1.95 mmol), sulfanilamide (0.362 g, 2.10 mmol) and HATU (0.798 g, 2.10 mmol) in DMF (10 mL) and Et3N (1.0 mL) was stirred at 40° C. overnight. The reaction mixture was purified by flash chromatography over silica gel eluting with MeOH/DCM to give tert-butyl 2-((6-oxo-6-(4-sulfamoylphenylamino)hexyl)(pyridin-2-ylmethyl)amino)acetate (297 mg, 31%). ESMS m/z: 491.3 (M+H)+.

Workup

  1. customThe reaction mixture was purified by flash chromatography over silica gel eluting with MeOH/DCM

Sources & evidence

ORD record
ord-6b5c7f22a4c84dd6a43f8b48743d0283
Source dataset
uspto-grants-2012_07
Patent number
US08211402B2

Reaction notes

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