HCID 15409145, 화합물 → HCID 15409146, 화합물

HRID 1416239노트

반응식

HRID 1416239 반응식
[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

참가 물질

3

반응물 1

HCID 15409145HCID 15409145, 화합물

생성물 1

HCID 15409146HCID 15409146, 화합물수율 15.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2599795742fe44b7b4561b060ae289c3
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912246

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