Diisopropylcarbodiimide → HCID 22103815, compound

HRID 1457223Notes

Reaction equation

HRID 1457223 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29][NH:30][CH3:31])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])[O:4][N:3]=1.[NH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[C:33]1[C:41]([OH:43])=O.C(N=C=NC(C)C)(C)C>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[O:25][CH:26]=[CH:27][N:28]=3)=[CH:20][C:19]=2[CH2:29][N:30]([CH3:31])[C:41]([C:33]2[NH:32][C:40]3[C:35]([CH:34]=2)=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:43])(=[O:11])=[O:10])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 72899Indole-2-carboxylic acidHCID 22103549HCID 22103549, compound

Product 1

HCID 22103815HCID 22103815, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.05 g (0.114 mmol) of N-(3,4-dimethyl-5-isoxazolyl)-2'-[(methylamino)methyl]-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide prepared as described in step A of Example 28 in 2 mL of CH2Cl2 and 0.1 mL DMF, 0.018 g (0.114 mmol) of indole-2-carboxylic acid and 0.021 g (0.142 mmol) of 1,3-diisopropylcarbodiimide were added. The mixture was then stirred at room temperature for 12 hr and evaporated. The residue was purified by reverse phase preparative HPLC on a 30×500 mm ODS S10 column using 80% solvent B (90% MeOH, 10% H2O, 0.1% TFA) and 20% solvent A (10% MeOH, 90% H2O, 0.1% TFA). The appropriate fractions were collected and neutralized with aqueous sodium bicarbonate to pH 7 and concentrated to 10 mL. The solution was then acidified to pH 4 using aqueous sodium bisulfate and the white solid was filtered and dried to provide 0.024 g (36%) of the title compound of this Example as a white solid. m.p. 135°-145° C.

Workup

  1. customevaporated
  2. customThe residue was purified by reverse phase preparative HPLC on a 30×500 mm ODS S10 column
  3. customThe appropriate fractions were collected
  4. concentrationconcentrated to 10 mL
  5. filtrationthe white solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-92f9ce99c4174784b87fa4567fcb975b
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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