Pyridine → HCID 59472939, compound

HRID 1678794Notes

Reaction equation

HRID 1678794 reaction equation
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:7]([C:13]1[CH:27]=[CH:26][C:16]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].N1C=CC=CC=1.[Cl:40][CH2:41][C:42](OC(=O)CCl)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:40][CH2:41][C:42]1[N:12]2[C:3]([C:4]3[CH:5]=[C:6]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:7]([C:13]4[CH:14]=[CH:15][C:16]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:26][CH:27]=4)=[N:8][C:9]=3[CH:10]=[CH:11]2)=[N:1][N:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 10946Chloroacetic anhydride2×HCID 59472955HCID 59472955, compound

Product 1

HCID 59472939HCID 59472939, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 16-2 (1.2 g, 2.7 mmol) in CH2Cl2 (10 ml) was added DMAP (0.03 g, 0.03 mmol) and pyridine (0.4 ml, 5.4 mmol) followed by chloroacetic anhydride (0.5 g, 3.0 mmol). The reaction mixture was stirred at room temperature for 2 h before adding additional chloroacetic anhydride (0.2 g, 0.9 mmol). After stirring for an additional 10 min the solvent was removed in vacuo. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc (3×30 ml). The combined organic layers were washed with water, brine and dried (Na2SO4/MgSO4). Removal of the solvent afforded the desired product 26-1 as a red powder. MS calculated: 500.2. Found 500.1

Workup

  1. stirringAfter stirring for an additional 10 min the solvent
  2. customwas removed in vacuo
  3. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc (3×30 ml)
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried (Na2SO4/MgSO4)
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-d248de2c5b144f31967504f8c1e192c3
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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