HCID 15409145, compound → HCID 15409146, compound

HRID 1416239Notes

Reaction equation

HRID 1416239 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)=O)[N:10]=2)[CH:7]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)[N:10]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 15409145HCID 15409145, compound

Product 1

HCID 15409146HCID 15409146, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1-[(6-chloroimidazo[1,2-a]pyridin-2-yl)carbonyl]-4-(4-methoxy-phenyl)piperazine (0.182 g) in THF (6 mL) is added borane-methyl sulfide complex (Aldrich; 0.14 mL). Additional THF (4 mL) is added and the mixture is stirred overnight, after which it is quenched with the dropwise addition of methanol. The mixture is concentrated under reduced pressure and then acetone/6N HCl (10/1) is added. The resulting mixture is stirred for 40 min and then concentrated under reduced pressure. The residue is partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are filtered through sodium sulfate, concentrated, and the residue chromatographed on silica gel using methanol/dichloromethane (2/98 to 4/96) to give 0.027 g of the title compound; mp 111-112° C.; IR (mineral oil) 1512, 1254, 1498, 1035, 830 cm-1. 1H NMR (CDCl3) δ2.74, 3.13, 3.76, 3.77, 6.82, 6.90, 7.12, 7.52, 7.54, 8.13.

Workup

  1. customafter which it is quenched with the dropwise addition of methanol
  2. concentrationThe mixture is concentrated under reduced pressure
  3. additionacetone/6N HCl (10/1) is added
  4. stirringThe resulting mixture is stirred for 40 min
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is partitioned between dichloromethane and aq. sodium bicarbonate
  7. filtrationThe organic layers are filtered through sodium sulfate
  8. concentrationconcentrated
  9. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-2599795742fe44b7b4561b060ae289c3
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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