Citric Acid → HCID 69662937, compound

HRID 1182437Notes

Reaction equation

HRID 1182437 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[S:12]([NH2:15])(=[O:14])=[O:13].[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Br:37])[C:25]=1[O:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH:34]([CH3:36])[CH3:35])[CH:28]=1)[C:20](O)=[O:21].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C1C=CC2N(O)N=NC=2C=1.CN(C)C=O>[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Br:37])[C:25]=1[O:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH:34]([CH3:35])[CH3:36])[CH:28]=1)[C:20]([C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[OH:1])[C:7]=1[S:12]([NH2:15])(=[O:13])=[O:14])=[O:21]

Participants

9

Reactant 5

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 870315-Hydroxynaphthalene-1-sulphonamideHCID 2724699PyBOPHCID 9932398HCID 9932398, compound

Product 1

HCID 69662937HCID 69662937, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 757711-HydroxybenzotriazoleCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent5×

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of 5-hydroxy-1-naphthalenesulphonamide (0.175 mmol) in dichloromethane (0.2 ml) was added a solution of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)benzoic acid (0.035 mmol), DIEA (0.175 mmol) and dichloromethane (0.2 ml), dimethyl formamide was added to the solution if the sulphonamide not dissolved completely in dichloromethane. After 15 minutes PyBOP (0.042 mmol) and HOBt (0.001 mmol) in dichloromethane (0.3 ml) was added. The reaction mixture was heated at 50° C. for 20 hours. After cooling to room temperature, dichloromethane (1 ml) and citric acid solution (5%, 1 ml) was added and stirred vigorously for 30 min. The organic phase was dried, concentrated and the residue was finally subjected to semi-preparative HPLC (Silica column: 250×20 mm, ethyl acetate/n-heptane (both with 0.5% acetic acid). Gradient: first 2 min 15% ethyl acetate, then over 13 min to 100% ethyl acetate, then additional 5 min 100% ethyl acetate) to give 12 mg (54%) of the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-95a28253b43248a28c7dcf50311b2467
Source dataset
uspto-grants-2007_10
Patent number
US07288571B2

Reaction notes

Loading…