Taurine → HCID 86662221, compound

HRID 1627262Notes

Reaction equation

HRID 1627262 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][C:26]=3[F:34])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:35][CH3:36].S(Cl)(Cl)=O.[NH2:41][CH2:42][CH2:43][S:44]([OH:47])(=[O:46])=[O:45].[CH3:48][CH2:49][N:50]([CH2:53][CH3:54])[CH2:51][CH3:52]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[CH:33]=[CH:32][C:28]([C:29]([NH:41][CH2:42][CH2:43][S:44]([O-:47])(=[O:46])=[O:45])=[O:30])=[CH:27][C:26]=3[F:34])=[N:13][CH:12]=2)([CH3:9])[CH3:10])=[CH:4][C:3]=1[O:35][CH3:36].[CH2:49]([NH+:50]([CH2:53][CH3:54])[CH2:51][CH3:52])[CH3:48]

Participants

6

Reactant 4

HCID 1123TaurineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 66739996HCID 66739996, compound

Product 1

HCID 86662221HCID 86662221, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3-fluorobenzoic acid (50 mg, 0.095 mmol) in DCM (3 mL) was added thionyl chloride (14 μL, 0.19 mmol) at 0° C. After reluxing for 13 h, the reaction mixture was cooled to room temperature and concentrated in vacuo. The crude material was dissolved in DCM (3 mL). To this solution were added taurine (12.4 mg, 0.099 mmol) and Et3N (26 μL, 0.19 mmol). The mixture was stirred for 5 h at room temperature and concentrated in vacuo. The crude residue was triturated with EtOAc (10 mL), and filtered through Celite™. The filtrate was concentrated in vacuo and was purified by chromatography (silica, DCM-MeOH=10:1) to afford triethylammonium 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3-fluorobenzamido)ethanesulfonate (45 mg, 65%) as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.54-7.47 (m, 2H), 7.27 (s, 1H), 7.15 (d, 1H), 7.06 (t, 1H) 6.81-6.77 (m, 2H), 6.48-6.45 (m, 2H), 6.06-6.03 (m, 2H), 4.04 (s, 2H), 3.85 (t, 2H), 3.69 (s, 3H), 3.24 (q, 6H), 3.13 (t, 2H), 1.50 (s, 6H), 1.33 (t, 9H); MS (EI) m/z 637 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude material was dissolved in DCM (3 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was triturated with EtOAc (10 mL)
  5. filtrationfiltered through Celite™
  6. concentrationThe filtrate was concentrated in vacuo
  7. customwas purified by chromatography (silica, DCM-MeOH=10:1)

Sources & evidence

ORD record
ord-eb11a312535c48ac9f7477a4599e2452
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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