Diisopropylcarbodiimide → HCID 22103772, compound

HRID 1457203Notes

Reaction equation

HRID 1457203 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.[F:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[F:42])[C:36]([OH:38])=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:36](=[O:38])[C:35]2[CH:39]=[CH:40][C:41]([F:42])=[C:33]([F:32])[CH:34]=2)(=[O:11])=[O:10])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 991663,4-Difluorobenzoic acidHCID 22103549HCID 22103549, compound

Product 1

HCID 22103772HCID 22103772, 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 3,4-difluorobenzoic acid (10.8 mg, 0.068 mmol) in 0.68 ml of CH2Cl2 and 0.1 ml DMF, 1,3-diisopropylcarbodiimide (9.5 mg, 0.075 mmol) was added. The reaction was stirred at room temperature for 5 hrs and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 19% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 81% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (22 mg, 56%) as a white solid, m.p. 122°-128° C. (amorphous).

Workup

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

Sources & evidence

ORD record
ord-119eb2cafc0b4200a917617d82ffe6ef
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

Loading…