Water → [5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-chloro-benzyl)-amine

HRID 2261562노트

반응식

HRID 2261562 반응식
C(OC(=O)[N:7]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:24]2[C:32]3[C:27](=[N:28][CH:29]=[C:30]([Br:33])[CH:31]=3)[NH:26][CH:25]=2)O)=[CH:18][N:17]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>C(#N)C>[Br:33][C:30]1[CH:31]=[C:32]2[C:24]([CH2:22][C:19]3[CH:20]=[CH:21][C:16]([NH:7][CH2:8][C:9]4[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=4)=[N:17][CH:18]=3)=[CH:25][NH:26][C:27]2=[N:28][CH:29]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59593354(5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl)-(4-chloro-benzyl)-carbamic acid tert-butyl ester

생성물 1

HCID 59593278[5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-chloro-benzyl)-amine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To {5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl}-(4-chloro-benzyl)-carbamic acid tert-butyl ester (45, 180.0 mg, 0.33 mmol) in acetonitrile (30.0 mL) were added trifluoroacetic acid (2.0 mL, 0.026 mol) and triethylsilane (4.0 mL, 0.025 mol). The reaction was heated to reflux for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography eluting with 10% methanol in dichloromethane to give compound (P-0038, 120 mg, 85.2%). MS (ESI)[M+H+]+=427.2, 429.2.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 10% methanol in dichloromethane
  9. customto give compound (P-0038, 120 mg, 85.2%)

출처 및 근거

ORD 기록
ord-bc126e62187348e7a2fcf9c2769195f8
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846941B2

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