2,4-Difluorophenyl isocyanate → HCID 86659760, compound

HRID 1889630Notes

Reaction equation

HRID 1889630 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][CH:33]=1)[CH2:6][N:7]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[S:8]([C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:12]=1[OH:19])(=[O:10])=[O:9].[F:34][C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=1[N:42]=[C:43]=[O:44]>CN(C=O)C>[Cl:18][C:13]1[C:12]([OH:19])=[C:11]([S:8]([N:7]([CH2:6][C:5]2[CH:31]=[CH:32][CH:33]=[C:3]([CH2:2][NH:1][C:43]([NH:42][C:36]3[CH:37]=[CH:38][C:39]([F:41])=[CH:40][C:35]=3[F:34])=[O:44])[CH:4]=2)[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=2)(=[O:9])=[O:10])[CH:16]=[C:15]([Cl:17])[CH:14]=1

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 58531583HCID 58531583, compound

Product 1

HCID 86659760HCID 86659760, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-(aminomethyl)benzyl)-3,5-dichloro-2-hydroxy-N-(4-(trifluoromethyl)benzyl)benzenesulfonamide (40 mg, 0.08 mmol) in DMF (2 mL) was added 2,4-difluorophenyl isocyanate (10.0 μL, 0.09 mmol). The resulting mixture was stirred at rt for 3 h under nitrogen. The mixture was concentrated and purified by preparative HPLC. Fractions containing the desired product were combined, concentrated and lyophilized to give a white solid (30 mg, 57%). 1H NMR (CD3OD): δ 7.59 (d, J=2.8 Hz, 1H), 7.52 (d, J=2.2 Hz, 1H), 7.48 (d, J=7.7 Hz, 2H), 7.44 (d, J=8.8 Hz, 2H), 7.39-7.37 (m, 4H), 7.31 (t, 7.7 Hz, 2H), 7.24 (d, J=7.7 Hz, 2H), 7.19 (t, J=7.1 Hz, 2H), 7.09 (m, 2H), 7.02 (s, 1H), 6.89 (d, J=6.6 Hz, 1H), 4.48 (s, 2H), 4.40 (s, 2H), 4.23 (s, 2H); MS (ESI): (M+H)+=714.2.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC
  3. additionFractions containing the desired product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-19938fabaa4f4b95a6257c65419958ad
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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