Water → (S)-1-(6-iodobenzo[d]thiazol-2-yl)pyrrolidin-3-ol

HRID 2040958노트

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HRID 2040958 반응식
[I:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7](S(C)(=O)=O)[S:8][C:4]=2[CH:3]=1.[NH:15]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[I:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([N:15]3[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16]3)[S:8][C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2733874(3S)-pyrrolidin-3-olHCID 669061396-Iodo-2-(methylsulfonyl)benzo[d]thiazole

생성물 1

HCID 66905790(S)-1-(6-iodobenzo[d]thiazol-2-yl)pyrrolidin-3-ol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

A stirred mixture of 6-iodo-2-(methylsulfonyl)benzo[d]thiazole (Reference Example 6c, 1.50 g, 4.42 mmol), (S)-pyrrolidin-3-ol (0.500 g, 5.74 mmol), and potassium carbonate (1.222 g, 8.84 mmol) in N,N-dimethylformamide (21.5 mL) was heated to 150° C. under microwave irradiation for 10 minutes. The reaction mixture was cooled to room temperature, then poured into water (350 mL) to give a precipitate. The precipitate was collected by filtration, rinsed with water, and then dissolved in ethyl acetate. The ethyl acetate solution was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give a crude solid that was purified by silica gel chromatography (100% CHCl3 to 97:3 CHCl3/methanol). Fractions containing product were combined an concentrated under reduced pressure to provide (S)-1-(6-iodobenzo[d]thiazol-2-yl)pyrrolidin-3-ol. 1H NMR (300 MHz, CD3OD) δ ppm 2.03-2.14 (m, 1H), 2.15-2.29 (m, 1H), 3.47-3.55 (m, 1H), 3.58-3.75 (m, 3H), 4.53-4.59 (m, 1H), 7.23 (d, J=8 Hz, 1H), 7.53-7.59 (m, 1H), 7.95-7.98 (m, 1H); MS (DCI/NH3) m/z 347 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto give a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washrinsed with water
  5. dissolutiondissolved in ethyl acetate
  6. dry with materialThe ethyl acetate solution was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a crude solid that
  10. customwas purified by silica gel chromatography (100% CHCl3 to 97:3 CHCl3/methanol)
  11. additionFractions containing product
  12. concentrationan concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ab0797c16f3145c5bf68283efdd06899
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580968B2

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