1,2-Dichloroethane → HCID 24987067, compound

HRID 552564Notes

Reaction equation

HRID 552564 reaction equation
CS(O)(=O)=O.CS(O)(=O)=O.[NH2:11][C@H:12]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:23][C:15]2[C:16]3[CH:17]=[N:18][NH:19][C:20]=3[CH:21]=[CH:22][C:14]=2[CH2:13]1.[CH3:32][N:33]1[C:37]2([CH2:46][CH2:45][C:44]3[C:39](=[CH:40][CH:41]=[C:42]([C:47](O)=[O:48])[CH:43]=3)[CH2:38]2)[C:36](=[O:50])[NH:35][C:34]1=[O:51].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH3:29][C:28]([CH3:31])([CH3:30])[CH2:27][N:24]1[C:25](=[O:26])[C@H:12]([NH:11][C:47]([C:42]2[CH:43]=[C:44]3[C:39](=[CH:40][CH:41]=2)[CH2:38][C:37]2([C:36](=[O:50])[NH:35][C:34](=[O:51])[N:33]2[CH3:32])[CH2:46][CH2:45]3)=[O:48])[CH2:13][C:14]2[CH:22]=[CH:21][C:20]3[NH:19][N:18]=[CH:17][C:16]=3[C:15]=2[CH2:23]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 18440315HCID 18440315, compoundHCID 86640002HCID 86640002, compound

Product 1

HCID 24987067HCID 24987067, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(R)-amino-9-(2,2-dimethylpropyl)-6,7,9,10-tetrahydro-3H-2,3,9-triazacyclohepta[e]inden-8-one bis-methanesulfonate (110 mg, 0.23 mmol) [Chaturvedula et al. WO 2006/052378], (±)-3-methyl-2,5-dioxo-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-6′-carboxylic acid (77 mg, 0.28 mmol) [Bell et al. WO 2004/082605], HOBT (43 mg, 0.28 mmol), and EDC (54 mg, 0.28 mmol) in DMF (2 mL) is stirred at ambient temperature for 18 h. The reaction mixture is purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H-90:10:0.1 to 5:95:0.1. The pure, product-containing fractions are combined and made basic with saturated aqueous NaHCO3. The resulting mixture is extracted with EtOAc (2×20 mL), and the combined organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound.

Workup

  1. customThe reaction mixture is purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions
  4. extractionThe resulting mixture is extracted with EtOAc (2×20 mL)
  5. washthe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c804b2815d054c8b8dd45fe395e42eca
Source dataset
uspto-grants-2011_05
Patent number
US07951795B2

Reaction notes

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