Phenylacetic Acid → HCID 11071765, compound

HRID 1457201Notes

Reaction equation

HRID 1457201 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.[C:32]1([CH2:38][C:39]([OH:41])=O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N=C=NC(C)C)(C)C>C(Cl)Cl>[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:39](=[O:41])[CH2:38][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)(=[O:11])=[O:10])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 12734DiisopropylcarbodiimideHCID 22103549HCID 22103549, compound

Product 1

HCID 11071765HCID 11071765, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N-(3,4-dimethyl-5-isoxazolyl)-2'-[(methylamino)methyl]-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide (30 mg, 0.068 mmol, prepared as described in Step (A) of Example 28) and benzeneacetic acid (8.5 mg, 0.062 mmol) in 0.6 ml of CH2Cl2, 1,3-diisopropylcarbodiimide (8.6 mg, 0.068 mmol) was added. The reaction was stirred at room temperature for 5.5 hrs and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 25% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 75% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (21 mg, 61%) as a white solid, m.p. 114°-122° C. (amorphous).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC on an ODS S10 column

Sources & evidence

ORD record
ord-a84250d140bd49d5871f516915796f1d
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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