1,2-Dichloroethane → HCID 9933560, compound

HRID 1865170Notes

Reaction equation

HRID 1865170 reaction equation
C([N:9]1[C:17]2[C:12](=[C:13]3[CH:20]([CH2:21][Cl:22])[CH2:19][N:18]([C:23]([O:25]C(C)(C)C)=O)[C:14]3=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31])(=O)C1C=CC=CC=1.Cl.C(Cl)CCl.[CH3:40][O:41][C:42]1[CH:43]=[C:44]2[C:48](=[CH:49][CH:50]=1)[NH:47][C:46](C(O)=O)=[CH:45]2>C(OCC)(=O)C>[Cl:22][CH2:21][CH:20]1[C:13]2=[C:12]3[C:17](=[CH:16][CH:15]=[C:14]2[N:18]([C:23]([C:46]2[NH:47][C:48]4[C:44]([CH:45]=2)=[CH:43][C:42]([O:41][CH3:40])=[CH:50][CH:49]=4)=[O:25])[CH2:19]1)[NH:9][C:10]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:11]3

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 204015-Methoxyindole-2-carboxylic acidHCID 10163016HCID 10163016, compound

Product 1

HCID 9933560HCID 9933560, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound 3.7(100 mg, 0.21 mmol) was treated with a solution of hydrochloric acid in ethyl acetate (4M, 500 μL). After 30 min, the solvent was concentrated and DMF (1 mL) was added. The solution was treated with EDC (120 mg, 0.63 mmol) and 5-methoxyindole-2-carboxylic acid (120 mg, 0.63 mmol). After 16 h, the solvent was removed under reduced pressure and the residue (the 6N-benzoyl protected precursor of compound 3.8) was dissolved in CH3OH (1 mL). A solution of NaOCH3 in CH3OH (2M, 100 μL) was then added and the solution stirred for 10 minutes. The solvent was removed and chromatography (SiO2, 10% ethyl acetate/hexanes) gave the product (3.8) (100 mg, 86%). FABMS (NBA/NaI) m/z 557 (M+H+ expected 557).

Workup

  1. concentrationthe solvent was concentrated
  2. additionDMF (1 mL) was added
  3. waitAfter 16 h
  4. customthe solvent was removed under reduced pressure
  5. dissolutionthe residue (the 6N-benzoyl protected precursor of compound 3.8) was dissolved in CH3OH (1 mL)
  6. additionA solution of NaOCH3 in CH3OH (2M, 100 μL) was then added
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-fa451d301a7c41298778b7bc8809bf08
Source dataset
uspto-grants-2009_12
Patent number
US07626026B2

Reaction notes

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