Sodium hydride → 1388893-18-2

HRID 525091노트

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HRID 525091 반응식
[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[S:20][CH:21]=[CH:22][C:15]=12>CN(C)C=O>[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][CH:6]([O:9][C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[S:20][CH:21]=[CH:22][C:15]=23)[CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 5980664-Chlorothieno[2,3-b]pyridineHCID 18702099trans-4-(Dimethylamino)cyclohexanol

생성물 1

HCID 681103201388893-18-2

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

Into a 50-mL round-bottom flask, was placed a solution of 4-(dimethylamino)cyclohexan-1-ol (127 mg, 0.89 mmol, 1.50 equiv) in N,N-dimethylformamide (15 mL). This was followed by the addition of sodium hydride (71 mg, 1.77 mmol, 3.00 equiv, 60%). The resulting solution was stirred for 30 minutes at 80° C. in an oil bath. 4-chlorothieno[2,3-b]pyridine (100 mg, 0.59 mmol, 1.00 equiv) was added to the mixture. The resulting solution was stirred for 3 h at 120° C. in an oil bath. The reaction was then quenched by the addition of 10 mL of ethanol. The resulting mixture was concentrated under vacuum. The residue was purified on a silica gel column with dichloromethane/methanol (10:1). The resulting product (50 mg) was further purified by Prep-HPLC with the following conditions: Column, SunFire Prep C18, 19*150 mm 5 um; mobile phase, CH3CN and water with 0.05% NH4HCO3 (3.0% water with 0.05% NH4HCO3 up to 3.0% in 1 min, up to 4.7.0% in 13 min, up to 100.0% in 2 min); Detector, uv 254/220 nm. This resulted in 9.6 mg (6%) of N,N-dimethyl-4-[thieno[2,3-b]pyridin-4-yloxy]cyclohexan-1-amine as a white solid.

후처리

  1. customInto a 50-mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for 3 h at 120° C. in an oil bath
  3. customThe reaction was then quenched by the addition of 10 mL of ethanol
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThe residue was purified on a silica gel column with dichloromethane/methanol (10:1)
  6. customThe resulting product (50 mg) was further purified by Prep-HPLC with the following conditions
  7. waitmobile phase, CH3CN and water with 0.05% NH4HCO3 (3.0% water with 0.05% NH4HCO3 up to 3.0% in 1 min
  8. waitup to 4.7.0% in 13 min
  9. waitup to 100.0% in 2 min)
  10. customThis resulted in 9.6 mg (6%) of N,N-dimethyl-4-[thieno[2,3-b]pyridin-4-yloxy]cyclohexan-1-amine as a white solid

출처 및 근거

ORD 기록
ord-8348ffdc63a54c06ae03081e0bc2ae4f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340554B2

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