Hydrochloric Acid → 3-{4-[5-(3,4-Difluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-benzooxazol-2-yl}-benzoic acid

HRID 1046950Notes

Reaction equation

HRID 1046950 reaction equation
C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]4[N:23]([C:24](=[O:34])[C:25]5[C:30]([F:31])=[CH:29][C:28]([F:32])=[CH:27][C:26]=5[F:33])[N:22]=[C:21]([C:35]5[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=5)[S:20]4)[C:13]=3[N:14]=2)[CH:5]=1.[Li+].[OH-].Cl>C1COCC1.CO>[F:42][C:37]1[CH:36]=[C:35]([C:21]2[S:20][CH:19]([C:15]3[C:13]4[N:14]=[C:10]([C:6]5[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=5)[C:3]([OH:43])=[O:2])[O:11][C:12]=4[CH:18]=[CH:17][CH:16]=3)[N:23]([C:24](=[O:34])[C:25]3[C:26]([F:33])=[CH:27][C:28]([F:32])=[CH:29][C:30]=3[F:31])[N:22]=2)[CH:40]=[CH:39][C:38]=1[F:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67279381HCID 67279381, compound

Product 1

HCID 580257643-{4-[5-(3,4-Difluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-benzooxazol-2-yl}-benzoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

3-{4-[5-(3,4-Difluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-benzooxazol-2-yl}-benzoic acid methyl ester (0.02 mmol) is dissolved in THF/MeOH (1 mL/0.5 mL) and treated with aqueous LiOH (1 M) (0.5 mL) at room temperature for 30 minutes. Aqueous HCl (3 M) is added to adjust the pH to 5-6. The solvent is removed and the residue is purified by preparative HPLC (20-100% MeCN/H2O) to yield 3-{4-[5-(3,4-difluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-benzooxazol-2-yl}-benzoic acid: 1H NMR (400 MHz, CDCl3) 8.95 (s, 1H), 8.48 (d, J=7.9 Hz, 1H), 8.27 (d, J=7.8 Hz, 1H), 7.92 (s, 1H), 7.66 (t, J=7.8 Hz, 1H), 7.6 (dd, J1=7.7 Hz, J2=1.2 Hz, 1H), 7.46 (m, 1H), 7.29-7.42 (m, 3H), 7.19 (q, J=8.2 Hz, 1H), 6.76-6.81 (m, 2H); LC/MS (ES+): (M+1) 596.0, (M+Na) 618.0.

Workup

  1. customThe solvent is removed
  2. customthe residue is purified by preparative HPLC (20-100% MeCN/H2O)

Sources & evidence

ORD record
ord-b6b9dac279fc45f48fc03e13bef298af
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

Loading…