4-Biphenylyl isocyanate → HCID 44594823, compound

HRID 1889631Notes

Reaction equation

HRID 1889631 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].[CH:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([N:46]=[C:47]=[O:48])=[CH:42][CH:41]=2)=[CH:36][CH:35]=1>CN(C=O)C>[C:40]1([C:37]2[CH:36]=[CH:35][CH:34]=[CH:39][CH:38]=2)[CH:41]=[CH:42][C:43]([NH:46][C:47](=[O:48])[NH:1][CH2:2][C:3]2[CH:4]=[C:5]([CH:31]=[CH:32][CH:33]=2)[CH2:6][N:7]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=2)[S:8]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:12]=2[OH:19])(=[O:9])=[O:10])=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 36123194-Biphenylyl isocyanateHCID 58531583HCID 58531583, compound

Product 1

HCID 44594823HCID 44594823, compoundYield 60%

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 (60 mg, 0.12 mmol) in DMF (3 mL) was added 4-biphenyl isocyanate (23.7 mg, 0.12 mmol). The resulting mixture was stirred at rt. for 2 h under nitrogen. The mixture was concentrated and dissolved in MeOH, purified by preparative HPLC. The fractions containing the desired product were combined, concentrated and lyophilized to give white solid (50 mg, 60%).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in MeOH
  3. custompurified by preparative HPLC
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-63dcbfe0ebfe4cd68d99a3ea72ae8bd4
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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