Chloroacetaldehyde → HCID 11245036, compound

HRID 916646Notes

Reaction equation

HRID 916646 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[N:18]=2)[N:5]=[C:4]([CH3:24])[N:3]=1.Cl[CH2:26][CH:27]=O>CN(C=O)C>[F:23][C:19]1[N:18]=[C:17]([C:13]2[N:12]([CH2:11][C:6]3[N:5]=[C:4]([CH3:24])[N:3]4[CH:26]=[CH:27][N:1]=[C:2]4[C:7]=3[CH2:8][CH2:9][CH3:10])[CH:16]=[CH:15][N:14]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 57503302HCID 57503302, compound

Product 1

HCID 11245036HCID 11245036, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 126 (1.2 mmol) and chloroacetaldehyde (1 mL) in DMF (10 ml) is heated at 70° C. in a sealed tube overnight. The solvent is removed in vacuo and water (15 ml) and EtOAc (15 ml) are added to the residue. The layers are separated and the aqueous layer is extracted with EtOAc (15 ml). The combined extracts are washed with brine (15 ml), dried (Na2SO4) and evaporated. PTLC separation of the residue with 10% MeOH in CH2Cl2 provides the title compound (119) as a white solid; LC-MS, M+1 351.1; 1H-NMR (CDCl3) δ: 8.10 (dd, 1H), 7.85 (q, 1H), 7.66 (d, 1H), 7.44 (d, 1H), 7.20 (d, 1H), 7.12 (d, 1H), 6.86 (dd, 1H), 6.02 (s, 2H), 3.01–3.07 (m, 2H), 2.69 (s, 3H), 1.60–1.67 (m, 2H), 0.94 (t, 3H).

Workup

  1. customThe solvent is removed in vacuo and water (15 ml) and EtOAc (15 ml)
  2. additionare added to the residue
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (15 ml)
  5. washThe combined extracts are washed with brine (15 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPTLC separation of the residue with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-f2e34cccf97741da9c20ef3853be83bc
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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