Chloroacetaldehyde → HCID 57683208, compound

HRID 2427290Notes

Reaction equation

HRID 2427290 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1([C:24](=[S:26])[NH2:25])[CH2:23][CH2:22]1.Cl[CH2:28][CH:29]=O>CN(C)C=O.O>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1([C:24]2[S:26][CH:28]=[CH:29][N:25]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 33ChloroacetaldehydeHCID 57683205HCID 57683205, compound

Product 1

HCID 57683208HCID 57683208, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 119 (100 mg, 0.24 mmol) and chloroacetaldehyde (22 mg, 0.28 mmol) in N,N-dimethylformamide (2 ml) was heated at 90° C. for 2 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with dichloromethane (×3). The combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was dissolved in acetonitrile (2 ml) and purified by automated preparative liquid chromatography (Gilson system, 150 mm×30 mm Phenomenex LUNA C18(2) 10 μm column) using an acetonitrile:water gradient [50:50 to 98:2]. The appropriate fractions were concentrated in vacuo to give the titled compound (10 mg).

Workup

  1. extractionextracted with dichloromethane (×3)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in acetonitrile (2 ml)
  5. custompurified
  6. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-ccfc2d0d6a1e445baf4eae3c7b76984c
Source dataset
uspto-grants-2011_06
Patent number
US07968584B2

Reaction notes

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