1,2-Dichloroethane → HCID 86669790, compound

HRID 1755181Notes

Reaction equation

HRID 1755181 reaction equation
[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[N:10]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:11]([CH:13]([CH2:24]C1C=CC(C2CCCCC=2)=CC=1)[CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1)=[O:12].[CH2:43](Cl)[CH2:44]Cl.[CH:47]1[CH:52]=[C:51]2N=NN(O)[C:50]2=[CH:49][CH:48]=1.O.[NH2:58][CH2:59][CH2:60][S:61]([OH:64])(=[O:63])=[O:62].[CH:65]([C:68](C(C)C)(NCC)[CH3:69])(C)[CH3:66]>CN(C=O)C>[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[N:10]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:11]([CH:13]([CH2:24][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[CH:44]1[CH2:43][CH2:69][CH2:68][CH:65]=[CH:66]1)[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:58][CH2:59][CH2:60][S:61]([OH:64])(=[O:63])=[O:62])=[O:21])=[CH:22][CH:23]=1)=[O:12]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 1123TaurineHCID 27960291-Hydroxybenzotriazole hydrateHCID 21936557DiisopropyldiethylamineHCID 67486669HCID 67486669, compound

Product 1

HCID 86669790HCID 86669790, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 4-[2-(4-Benzofuran-2-ylphenylcarbamoyl)-3-(4-cyclohex-1-enylphenyl)-propyl]-benzoic acid from step f above, EDC (101 mg, 0.53 mmol), HOBT hydrate (80 mg, 0.53 mmol), taurine (66 mg, 0.53 mmol) and diisopropyl diethylamine (0.18 mL, 1.1 mmol) in DMF (10 mL) was stirred at RT overnight. The solvent was removed under vacuum and 1N HCl was added. The resulting precipitate was filtered, washed with water and purified by preparatory HPLC on a Shimadzu modular HPLC system using a Waters Atlantis dC18 30×75 mm preparatory column and running a gradient from 40% to 100% acetonitrile over 13 minutes. TFA was used as an ionizer and was present in 0.05% (v/v). Detection was accomplished using an in-line UV detector running at 254 nm. Rotary evaporation of the solvated compound provided the title compound (50 mg): 1H NMR (300 MHz, DMSO-d6): δ 9.94 (s, 1H), 8.43 (t, J=6.12 Hz, 1H), 7.80 (d, J=8.4 Hz, 2H), 7.69 (d, J=8.4 Hz, 2H) 7.64-7.21 (m, 11H), 7.15 (d, J=8.4 Hz, 2H), 3.48 (dd, J=12.6 Hz, J=6.3 Hz, 2H), 3.1-2.9 (m, 3H), 2.8-2.4 (m, 4H), 2.38 (s, 1H), 2.35-2.25 (br m, 2H), 2.19-2.09 (br m, 2H), 1.77-1.67 (br m, 2H), 1.6-1.5 (br m, 2H). LC-MS m/z=661 [C349H38N2O6S+H]−.

Workup

  1. customThe solvent was removed under vacuum and 1N HCl
  2. additionwas added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. custompurified by preparatory HPLC on a Shimadzu modular HPLC system
  6. customover 13 minutes
  7. customRotary evaporation of the solvated compound

Sources & evidence

ORD record
ord-62a14172b5794b5594f3b4f0d822bff9
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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