1,2-Dichloroethane → HCID 11646588, compound

HRID 550409Notes

Reaction equation

HRID 550409 reaction equation
C(Cl)CCl.[NH:5]([C:7]1[C:8]2[N:9]([CH:17]=[CH:18][CH:19]=2)[C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH2:6].[C:20]([CH:27]([CH:31]([NH2:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:38])C(O)=O)(OC(C)(C)C)=[O:21].C(=O)(O)[O-].[Na+].C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.O>[CH:17]1[N:9]2[C:10]3[C:15]([N:16]=[C:7]([NH:5][NH:6][C:20](=[O:21])[CH2:27][CH:31]([NH2:39])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[Cl:38])[C:8]2=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 10679460HCID 10679460, compoundHCID 53445018HCID 53445018, compound

Product 1

HCID 11646588HCID 11646588, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of EDC (94 mg, 0.49 mmol) and DMAP (cat.) in ethyl acetate (15 mL), 4-hydrazinopyrrolo[1,2-a]quinoxaline 14a (77 mg, 0.39 mmol) and Boc-3-amino-3-(2-chlorophenyl)propionic acid (78 mg, 0.39 mmol) were added, portion wise over 15 minutes period. The resulting mixture was stirred at room temperature for 24 h, then shaken with sodium bicarbonate saturated solution and water. Evaporation of the dried extract gave a residue which was purified by crystallization and used for the subsequent hydrolytic step without further characterization. The solid obtained was added to a stirred mixture of TFA (2 mL) and anisole (2 mL) at 0° C. The reaction mixture was allowed to reach to room temperature and stirred for an additional 50 minutes. Evaporation of the volatiles by azeotropization with toluene (3×3 mL) gave the title compound as a solid.

Workup

  1. customEvaporation of the dried
  2. extractionextract
  3. customgave a residue which
  4. customwas purified by crystallization
  5. customThe solid obtained
  6. customto reach to room temperature
  7. stirringstirred for an additional 50 minutes
  8. customEvaporation of the volatiles by azeotropization with toluene (3×3 mL)

Sources & evidence

ORD record
ord-87754e44a33f4314bed2dfca8c7495ff
Source dataset
uspto-grants-2011_05
Patent number
US07947682B2

Reaction notes

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