1,2-Dichloroethane → HCID 67368390, compound

HRID 1948563Notes

Reaction equation

HRID 1948563 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[N:18][CH:19]=[C:20]([CH3:22])[CH:21]=3)=[CH:12][C:8]=2[C:9]([OH:11])=O)[CH:4]=[N:3]1.C(Cl)C[Cl:25].[CH:27]1[CH:28]=[CH:29][C:30]2[N:35](O)N=[N:33][C:31]=2[CH:32]=1.CN1C[CH2:42][O:41]CC1.CN([CH:47]=[O:48])C>>[ClH:25].[CH3:47][O:48][C:32]1[CH:27]=[CH:28][C:29]([CH2:30][NH:35][C:9](=[O:11])[C:8]2[CH:12]=[C:13]([C:16]3[CH:17]=[N:18][CH:19]=[C:20]([CH3:22])[CH:21]=3)[CH:14]=[CH:15][C:7]=2[C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)=[N:33][C:31]=1[O:41][CH3:42]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 58408400HCID 58408400, compound

Product 1

HCID 67368390HCID 67368390, compound

Procedure

To a mixture of the carboxylic acid (2-5, 0.060 g, 0.205 mmol, 1 equiv), EDC (0.059 g, 0.307 mmol, 1.5 equiv), HOBt (0.050 g, 0.327 mmol, 1.6 equiv) in DMF (1 mL), the hydrochloride salt of the amine (x-x, 0.054 g, 0.266 mmol, 1.3 equiv) was added followed by N-methylmorpholine (0.112 mL, 1.023 mmol, 5 equiv) and the reaction was stirred overnight at room temperature. The reaction was partitioned between EtOAc and saturated aqueous NaHCO3, washed with water, brine, dried over MgSO4, and concentrated by rotary evaporation. The crude product was purified by column chromatography on silica gel (EtOAc/hexanes) to provide 2-6 as a white solid which was converted to the HCl salt. Data for 2-6: HRMS [M+H] C25H25N5O3 calc'd 444.2030. found 444.2042.

Workup

  1. customThe reaction was partitioned between EtOAc and saturated aqueous NaHCO3
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude product was purified by column chromatography on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-362161ec31b74ec9b12ad2fcd92ff50c
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

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