Triethylamine → HCID 22103497, compound

HRID 1457194Notes

Reaction equation

HRID 1457194 reaction equation
Cl.[CH3:2][NH:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][CH:13]=[CH:14][N:15]=2)[CH:8]=[CH:7][C:6]=1[C:16]1[C:17]([S:22]([NH:25][C:26]2[O:30][N:29]=[C:28]([CH3:31])[C:27]=2[CH3:32])(=[O:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1.[F:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([OH:40])=O)=[CH:36][CH:35]=1.C(N(CC)CC)C.ON1C2N=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C>C(Cl)Cl>[CH3:31][C:28]1[C:27]([CH3:32])=[C:26]([NH:25][S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[O:12][CH:13]=[CH:14][N:15]=3)=[CH:10][C:5]=2[CH2:4][N:3]([CH3:2])[C:38](=[O:40])[C:37]2[CH:36]=[CH:35][C:34]([F:33])=[CH:42][CH:41]=2)(=[O:24])=[O:23])[O:30][N:29]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 12734DiisopropylcarbodiimideHCID 181649HOAtHCID 131720973HCID 131720973, compound

Product 1

HCID 22103497HCID 22103497, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2'-[(methylamino)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide, monohydrochloride (100 mg, 0.21 mmol, prepared as described in Step (A) of Example 28) and 4-fluorobenzoic acid (29.5 mg, 0.21 mmol) in 0.3 ml of CH2Cl2, triethylamine (43 mg, 0.42 mmol) and 1-hydroxy-7-azabenzotriazole (31.6 mg, 0.23 mmol) were added and followed by 1,3-diisopropylcarbodiimide (29.3 mg, 0.23 mmol). The reaction was stirred at room temperature for 3 hrs and concentrated. The residue was purified by preparative HPLC on an ODS S10 O column using 31% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 69% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (60 mg, 51%) as a white solid, m.p. 125°-135° C. (amorphous).

Workup

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

Sources & evidence

ORD record
ord-cec2325600684fdb814321c0fb682b6f
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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