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Phenyl isocyanate → 5'-Phenylaminocarbonylaminospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

HRID 841069
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HRID 841069 반응식
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[CH:12]=[C:13]2[CH2:19][C:18]3([CH:24]4[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]4)[CH2:20]3)[O:17][C:14]2=[N:15][CH:16]=1>O1CCCC1>[C:1]1([NH:7][C:8]([NH:10][C:11]2[CH:12]=[C:13]3[CH2:19][C:18]4([CH:24]5[CH2:23][CH2:22][N:21]([CH2:26][CH2:25]5)[CH2:20]4)[O:17][C:14]3=[N:15][CH:16]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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참가 물질

4

반응물 2

HCID 7672Phenyl isocyanateHCID 15908236spiro[1-azabicyclo[2.2.2]octane-3,2'-3H-furo[2,3-b]pyridine]-5'-amine

생성물 1

HCID 100207835'-Phenylaminocarbonylaminospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under a nitrogen atmosphere, phenyl isocyanate (0.056 mL, 0.515 mmol) was added to a suspension of 5′-aminospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (119 mg, 0.514 mmol) in anhydrous tetrahydrofuran (5 mL) and stirred for 12 hours. The solvent was evaporated under reduced pressure and the residue purified by flash chromatography through silica gel, eluting with ammoniated chloroform/methanol (92.5:7.5), to obtain the title compound (155 mg, 0.442 mmol, 86%) as an off-white solid: electrospray MS (m/z, relative intensity) 351 ([MH]+, 100).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue purified by flash chromatography through silica gel
  3. washeluting with ammoniated chloroform/methanol (92.5:7.5)

출처 및 근거

ORD 기록
ord-1b0d805b21b74e9aa171f5144eac8298
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06369224B1

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