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Trifluoroacetic acid → 6-(4-Hydroxy-3-methoxy-5-methylaminomethyl-phenyl)-4-(1H-indol-2-yl)-2H-pyridazin-3-one

HRID 2234141
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HRID 2234141 반응식
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([CH2:29][NH:30][CH3:31])[C:26]([O:32]COCC[Si](C)(C)C)=[C:25]([O:41][CH3:42])[CH:24]=2)[N:20]=[N:19][C:18]=1[O:43]C)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:32][C:26]1[C:27]([CH2:29][NH:30][CH3:31])=[CH:28][C:23]([C:21]2[CH:22]=[C:17]([C:9]3[NH:8][C:16]4[C:11]([CH:10]=3)=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:18](=[O:43])[NH:19][N:20]=2)=[CH:24][C:25]=1[O:41][CH3:42]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 686384962-{3-Methoxy-6-[3-methoxy-5-methylaminomethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 1355131436-(4-Hydroxy-3-methoxy-5-methylaminomethyl-phenyl)-4-(1H-indol-2-yl)-2H-pyridazin-3-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
85 °C

실험 절차

118 mg of 2-{3-Methoxy-6-[3-methoxy-5-methylaminomethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester is dissolved in 5 ml of dichloromethane and 5 ml of trifluoroacetic acid and the solution is stirred for 4 h at RT. The solvents are removed under reduced pressure. The residue is dissolved in 26 ml of acetonitrile and 117 mg of potassium iodide and 76 mg of chlorotrimethylsilane are added. The reaction is heated to 85° C. for 3 h. The reaction is quenched by the addition of a drop of water, the solvent is removed under reduced pressure and the product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 13 mg. LC-MS (ES+) 377 (M+H)+.

후처리

  1. customThe solvents are removed under reduced pressure
  2. dissolutionThe residue is dissolved in 26 ml of acetonitrile
  3. addition117 mg of potassium iodide and 76 mg of chlorotrimethylsilane are added
  4. customThe reaction is quenched by the addition of a drop of water
  5. customthe solvent is removed under reduced pressure
  6. customthe product is purified by preparative RP-HPLC
  7. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-03fa61cdec1b4e5e9a5c2ed3bb883f33
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709466B2

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