Benzenepropanoic acid → HCID 10984658, compound

HRID 1457205Notes

Reaction equation

HRID 1457205 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]([OH:42])(=O)[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.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:32](=[O:42])[CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)(=[O:11])=[O:10])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 107Benzenepropanoic acidHCID 12734DiisopropylcarbodiimideHCID 22103549HCID 22103549, compound

Product 1

HCID 10984658HCID 10984658, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 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 hydrocinnamic acid (10.3 mg, 0.068 mmol) in 0.68 ml of CH2Cl2 and 0.08 ml of DMF, 1,3-diisopropylcarbodiimide (9.5 mg, 0.075 mmol) was added. The reaction was stirred at room temperature overnight and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 20% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 80% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (18 mg, 46%) as a white solid, m.p. 110°-117° C. (amorphous).

Workup

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

Sources & evidence

ORD record
ord-d596f6e45c9e4a8ba0500e6725c5175a
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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