Acetic Anhydride → 1-[4-(4-Fluoro-phenylamino)-5,7,8,9-tetrahydro-dipyrido[2,3-b;3',4'-d]pyrrol-6-yl]-ethanone

HRID 533768노트

반응식

HRID 533768 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]3[C:16]4[CH2:18][NH:19][CH2:20][CH2:21][C:15]=4[NH:14][C:13]=3[N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].C(N(CC)CC)C>ClCCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[C:17]3[C:16]4[CH2:18][N:19]([C:22](=[O:24])[CH3:23])[CH2:20][CH2:21][C:15]=4[NH:14][C:13]=3[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 46843141(4-Fluoro-phenyl)-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-yl)-amine

생성물 1

HCID 468437501-[4-(4-Fluoro-phenylamino)-5,7,8,9-tetrahydro-dipyrido[2,3-b;3',4'-d]pyrrol-6-yl]-ethanone수율 13.5%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

(4-Fluoro-phenyl)-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-yl)-amine (45 mg, 0.16 mmol), acetic anhydride (16 μL, 0.16 mmol), and triethylamine (66 μL, 0.48 mmol) were dissolved in 1,2-dichloroethane (2 mL), and stirred for 30 min at room temperature. The reaction was quenched with H2O, and the resulting material was filtered through an Extrelut column. The Extrelut column was washed with EtOAc, and the filtrate was concentrated. The crude material was purified via Biotage eluting with a gradient of 0 to 10% MeOH in DCM. Lyophilization of the purified product provided 62 (7 mg, 13% yield) as a oily residue. LC-MS (M+H=325, obsd.=325).

후처리

  1. customThe reaction was quenched with H2O
  2. filtrationthe resulting material was filtered through an Extrelut column
  3. washThe Extrelut column was washed with EtOAc
  4. concentrationthe filtrate was concentrated
  5. customThe crude material was purified via Biotage
  6. washeluting with a gradient of 0 to 10% MeOH in DCM

출처 및 근거

ORD 기록
ord-92c5224729e6488996087695b5d90434
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853391B2

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