Triethylamine → HCID 178453727, compound

HRID 2360294

Reaction equation

HRID 2360294 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH3:22])([CH2:15][CH:16]2CCNCC2)[C:12](=[O:14])[N:13]=1.[C:23]([NH:30][CH2:31][CH2:32][O:33][C:34]1[CH:42]=[CH:41][C:37](C(O)=O)=[CH:36][CH:35]=1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].CCN=C=NCCCN(C)C.C1C=CC2N([OH:63])N=NC=2C=1.[CH2:64]([N:66]([CH2:69][CH3:70])[CH2:67][CH3:68])C>C(Cl)Cl>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:15][CH:16]2[CH2:70][CH2:69][N:66]([C:64]([C:41]3[CH:42]=[C:34]([CH:35]=[CH:36][CH:37]=3)[O:33][CH2:32][CH2:31][NH:30][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:63])[CH2:67][CH2:68]2)([CH3:22])[C:12](=[O:14])[N:13]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27559974-(2-((tert-Butoxycarbonyl)amino)ethoxy)benzoic acidHCID 178422083HCID 178422083, compound

Product 1

HCID 178453727HCID 178453727, compoundYield 412.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-5-(piperidin-4-ylmethyl)thiazol-4(5H)-one (534 mg, 1.66 mmol), 4-[2-(Boc-amino)ethyloxy]-benzoic acid (NeoMPS, 701 mg, 2.49 mmol), EDCI (Aldrich, 637 mg, 3.32 mmol, 2.0 eq), HOBt (Aldrich, 45 mg, 0.332 mmol, 0.2 eq) and triethylamine (Aldrich, 336 mg, 3.32 mmol, 2.0 eq) in CH2Cl2 (10 mL) was stirred at room temperature for ca. 18 h. The reaction was quenched with saturated NaHCO3 (100 mL), and the crude product was extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Flash column chromatography (silica gel, 0-5% MeOH in CH2Cl2) afforded the title compound as a white solid (800 mg). MS (ESI, pos. ion) m/z: 585 (M+H).

Workup

  1. customThe reaction was quenched with saturated NaHCO3 (100 mL)
  2. extractionthe crude product was extracted with CH2Cl2 (3×100 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-641e630e461f4f2199d896e46929aacd
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Linked notes

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