Diisopropylethylamine → 2-(N-tert-butylsulfamoyl)-N-(2-carbamoylbiphenyl-3-yl)thiazole-4-carboxamide

HRID 2036850Notes

Reaction equation

HRID 2036850 reaction equation
[C:1]([NH:5][S:6]([C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:52]=1[C:63]([NH2:65])=[O:64]>C(Cl)Cl>[C:1]([NH:5][S:6]([C:9]1[S:10][CH:11]=[C:12]([C:14]([NH:50][C:51]2[C:52]([C:63](=[O:64])[NH2:65])=[C:53]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH:54]=[CH:55][CH:56]=2)=[O:16])[N:13]=1)(=[O:7])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669655723-Aminobiphenyl-2-carboxamideHCID 670559302-(N-tert-butylsulfamoyl)thiazole-4-carboxylic acid

Product 1

HCID 670559462-(N-tert-butylsulfamoyl)-N-(2-carbamoylbiphenyl-3-yl)thiazole-4-carboxamideYield 17.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(N-tert-butylsulfamoyl)thiazole-4-carboxylic acid (0.56 g, 2.1 mmol) in DCM (50 mL) was added HATU (1.41 g, 2.8 mmol) and DIPEA (1.04 ml, 5.6 mmol). The reaction mixture was stirred at room temperature for 1 h and then 3-aminobiphenyl-2-carboxamide (from example 218, 0.3 g, 1.4 mmol) was added. The resulting solution was stirred for an additional 16 h. After this time, the reaction mixture was washed with water, dried, filtered and concentrated under reduced pressure to yield a residue. The residue was purified by silica gel chromatography (30% EtOAc in hexane) to provide 2-(N-tert-butylsulfamoyl)-N-(2-carbamoylbiphenyl-3-yl)thiazole-4-carboxamide (0.11 g, 17% yield) as white solid. LCMS Method V: retention time 1.85 min; [M+1]=459.2.

Workup

  1. stirringThe resulting solution was stirred for an additional 16 h
  2. washAfter this time, the reaction mixture was washed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a residue
  7. customThe residue was purified by silica gel chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-73f59fb635234f5cabb47ffd70a4eb74
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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