4-Chlorobenzoic Acid → HCID 22103776, compound

HRID 1457198Notes

Reaction equation

HRID 1457198 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[CH:6][C:5]=1[C:15]1[C:16]([S:21]([NH:24][C:25]2[O:29][N:28]=[C:27]([CH3:30])[C:26]=2[CH3:31])(=[O:23])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=1.[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=O)=[CH:35][CH:34]=1.C(N=C=NC(C)C)(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([C:37]([N:2]([CH2:3][C:4]2[CH:9]=[C:8]([C:10]3[O:11][CH:12]=[CH:13][N:14]=3)[CH:7]=[CH:6][C:5]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21]([NH:24][C:25]2[O:29][N:28]=[C:27]([CH3:30])[C:26]=2[CH3:31])(=[O:22])=[O:23])[CH3:1])=[O:39])=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 63184-Chlorobenzoic AcidHCID 12734DiisopropylcarbodiimideHCID 22103549HCID 22103549, compound

Product 1

HCID 22103776HCID 22103776, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2'-[(methylamino)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide (24.1 mg, 0.055 mmol, prepared as described in Step (A) of Example 28) and 4-chlorobenzoic acid (7.8 mg, 0.05 mmol) in 0.5 ml of CH2Cl2, 4-dimethylaminopyridine (6.7 mg, 0.055 mmol) was added and followed by 1,3-diisopropylcarbodiimide (6.9 mg, 0.055 mmol). The reaction was stirred at room temperature for 18 hrs and concentrated. The residue was dissolved in MeOH, neutralized to pH>8 with aq. NaHCO3, and filtered. The filtrate was acidified to pH<5 with NaHSO4, and filtered to provide the title compound of this Example (18 mg, 62%) as a white solid, m.p. 122°-132° C. (amorphous).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in MeOH
  3. filtrationfiltered
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a15d3bb8f7b3452eaadcad6eddd79b83
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

Loading…