Dichloromethane → HCID 86603110, compound

HRID 855426Notes

Reaction equation

HRID 855426 reaction equation
[F:1][C:2]1[C:10]([C:11]([OH:13])=O)=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:14]([C:18]1[CH:33]=[CH:32][C:21]([CH2:22][NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(Cl)Cl.CCN=C=NCCCN(C)C.Cl>>[C:14]([C:18]1[CH:33]=[CH:32][C:21]([CH2:22][N:23]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:11]([C:10]2[C:2]([F:1])=[CH:3][CH:4]=[C:5]3[C:9]=2[NH:8][CH:7]=[CH:6]3)=[O:13])=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4559933(4-Tert-butyl-benzyl)-phenethyl-amineHCID 117081616-fluoro-1H-indole-7-carboxylic Acid

Product 1

HCID 86603110HCID 86603110, compoundYield 54.4%

Procedure

To a solution of 89 mg (0.5 mmol) of 6-fluoro-1H-indole-7-carboxylic acid and 134 mg (0.3 mmol) of (4-tert-butyl-benzyl)-phenethyl-amine in 5 ml DCM 105 mg (0.55 mmol) of EDC.HCl were added and the reaction mixture was stirred over night at rt. The solvent was evaporated and the residue was partitioned between diethyl ether/EtOAc and 1N aqueous HCl solution. A white solid precipitated. The reaction mixture was filtered and the organic layer was washed twice with 1N aqueous HCl solution, once with 2N aqueous NaOH solution and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave 70 mg (33%) product as a colorless oil. MS (ISP) 429.4 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between diethyl ether/EtOAc and 1N aqueous HCl solution
  3. customA white solid precipitated
  4. filtrationThe reaction mixture was filtered
  5. washthe organic layer was washed twice with 1N aqueous HCl solution, once with 2N aqueous NaOH solution and once with saturated aqueous NaCl solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-eb26453aa0be403dab066b90a6d10307
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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