Sulfanilamide → HCID 59850047, compound

HRID 215905Notes

Reaction equation

HRID 215905 reaction equation
[S:1]([NH2:11])(=[O:10])([C:3]1[CH:8]=[CH:7]C(N)=[CH:5][CH:4]=1)=[O:2].CN([P+](ON1N=NC2[C:24]1=[CH:25][CH:26]=[CH:27]C=2)(N(C)C)N(C)C)C.[F:32][P-](F)(F)(F)(F)F.[CH2:39]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH3:40].[CH3:46][N:47]([CH:49]=[O:50])C>C(Cl)Cl>[F:32][C:27]1[CH:26]=[CH:25][CH:24]=[C:42]2[C:43]=1[CH:40]=[CH:39][N:41]2[C@H:44]([CH3:45])[C:49]([NH:47][C:46]1[CH:5]=[CH:4][C:3]([S:1](=[O:2])(=[O:10])[NH2:11])=[CH:8][CH:7]=1)=[O:50]

Participants

6

Reactant 4

HCID 5333SulfanilamideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 59850047HCID 59850047, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2R-2-(4-fluoroindol-1-yl)propionic acid (1.2 g, 5.8 mmol), sulfanilamide (2 g, 11.6 mmol), BOP-reagent (2.6 g, 5.8 mmol), triethylamine (2.4 mL, 17.4 mmol) in DMF and CH2Cl2 (10 mL) was stirred under an N2 atmosphere at rt for 19 h. After evaporating the solvents under reduced pressure, the residue was purified by silica gel chromatography using 3% methanol in CH2Cl2, which gave (R)-2-(4-fluoro-1H-indol-1-yl)-N-(4-sulfamoyl phenyl)propanamide as a white solid. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=362.4; tR=2.78 min. 1H NMR (400 MHz, DMSO-d6) δ 7.50 (d, J=7.0 Hz, 2H), 7.42 (d, J=3.4 Hz, 1H), 7.08 (t, J=4.0 Hz, 2H), 6.85-6.79 (m, 1H), 6.57 (d, J=8.8 Hz, 2H), 6.51 (d, J=3.3 Hz, 1H), 6.19 (s, 2H), 5.17 (q, J=7.1 Hz, 1H), 1.62 (d, J=7.1 Hz, 3H).

Workup

  1. customAfter evaporating the solvents under reduced pressure
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ebe910b167a442058c1d95590ebea8bb
Source dataset
uspto-grants-2012_06
Patent number
US08193194B2

Reaction notes

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