Methanol → 1-Benzothiazol-6-yl-3-(4-morpholin-4-ylmethyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80238

반응식

HRID 80238 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[S:7]1[C:11]2[CH:12]=[C:13]([N:16]3[CH2:20][CH2:19][N:18]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][C:26]=4[CH:27]=O)[C:17]3=[O:29])[CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1.CO>C(O)(=O)C.C(Cl)(Cl)Cl>[S:7]1[C:11]2[CH:12]=[C:13]([N:16]3[CH2:20][CH2:19][N:18]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][C:26]=4[CH2:27][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[C:17]3=[O:29])[CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1

참가 물질

6

반응물 3

HCID 887MethanolHCID 8083MorpholineHCID 596362723-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridine-4-carbaldehyde

생성물 1

HCID 498726521-Benzothiazol-6-yl-3-(4-morpholin-4-ylmethyl-pyridin-3-yl)-imidazolidin-2-one수율 20.6%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6212Chloroform용매

실험 절차

Morpholine (0.032 mL, 0.3699 mmol) was added to a stirred solution of 3-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridine-4-carbaldehyde (I-177b: 100 mg, 0.3082 mmol) in acetic acid (2 mL) and stirred at room temperature for 4 hours. This was followed by the addition of NaBH (OAc)3 (98 mg, 0.4624 mmol). The resulting reaction mass was stirred at room temperature for 24 hours. The reaction was monitored by TLC (10% methanol in chloroform). The reaction mixture was concentrated under reduced pressure, added ice, basified using saturated NaHCO3 solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (2% methanol in chloroform) followed by preparative HPLC afforded 25 mg of the product (20.6% yield).

후처리

  1. customThe resulting reaction mass
  2. stirringwas stirred at room temperature for 24 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionadded ice
  5. extractionextracted
  6. washThe organic layer was washed with water, brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customPurification by column chromatography on silica gel (2% methanol in chloroform)

출처 및 근거

ORD 기록
ord-3a45abc6bdbd417d81106fa7713602a6
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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