Triethylamine → 3-Benzo[1,3]dioxol-5-yl-2-(6-hydroxy-benzofuran-2-carbonyl)-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

HRID 988313

반응식

HRID 988313 반응식
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[CH:6]=[C:7]([C:9]([OH:11])=O)[O:8][C:4]=2[CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([CH:29]3[C:33]4[NH:34][C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=5[C:41](=[O:42])[C:32]=4[CH2:31][NH:30]3)=[CH:23][C:22]=2[O:21]1.C(N(CC)CC)C>O1CCCC1.CN(C=O)C.CN(C)C1C=CN=CC=1>[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([CH:29]3[C:33]4[NH:34][C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=5[C:41](=[O:42])[C:32]=4[CH2:31][N:30]3[C:9]([C:7]3[O:8][C:4]4[CH:3]=[C:2]([OH:1])[CH:13]=[CH:12][C:5]=4[CH:6]=3)=[O:11])=[CH:23][C:22]=2[O:21]1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 108921213-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]quinolin-9-oneHCID 155315746-Hydroxy-1-benzofuran-2-carboxylic acid

생성물 1

HCID 118126473-Benzo[1,3]dioxol-5-yl-2-(6-hydroxy-benzofuran-2-carbonyl)-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
25 °C

실험 절차

To a solution of 6-hydroxy-2-benzofuranoic acid (0.054 g, 0.3 mmol) in tetrahydrofuran (5 mL) at 0° C. was added dropwise oxalyl chloride (0.046 g, 0.36 mmol) followed by DMF (2 drops). The solution was warmed to 25° C. and stirred for 30 min, then concentrated in vacuo. The residue was dissolved in tetrahydrofuran (5 mL), and added to a solution of 1,2,3,4-tetrahydro-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one (0.092 g, 0.3 mmol) (prepared as in Example 5) in THF (5 ml), triethylamine (0.045 g, 0.45 mmol) and 4-dimethylaminopyridine (0.01 g, cat.). The solution was stirred for 20 h at 25° C., and then concentrated in vacuo. The resulting crude residue was purified by silica gel column chromatography, eluting with 3% methanol in dichloromethane, to yield the product as a clear oil.

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in tetrahydrofuran (5 mL)
  3. stirringThe solution was stirred for 20 h at 25° C.
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude residue was purified by silica gel column chromatography
  6. washeluting with 3% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-d5ca64bb84704dfa9f1f414297fbd995
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06635638B2

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