Triethylamine → HCID 22103707, compound

HRID 1457196Notes

Reaction equation

HRID 1457196 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.C(N(CC)CC)C.[F:40][C:41]1[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=1)[C:44](Cl)=[O:45]>>[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:44](=[O:45])[C:43]2[CH:47]=[CH:48][CH:49]=[C:41]([F:40])[CH:42]=2)(=[O:24])=[O:23])[O:30][N:29]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 743763-Fluorobenzoyl chlorideHCID 131720973HCID 131720973, compound

Product 1

HCID 22103707HCID 22103707, compound

Procedure

To 2'-[(methylamino)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide, monohydrochloride (25 mg, 0.053 mmol, prepared as described in Step (A) of Example 28), triethylamine (13.3 mg, 0.13 mmol) was added and followed by 3-fluorobenzoyl chloride (8.3 mg, 0.053 mmol). The reaction was stirred at room temperature overnight and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 29% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 71% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (18 mg, 61%) 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 column

Sources & evidence

ORD record
ord-0466d0346d8f4ebfb1afff6cf2d9aeb0
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

Loading…