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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Trifluoroacetic acid → 1-(3-(Dimethylphosphoryl)phenyl)-3-(3-fluoro-4-(2-(5-((2-methoxyethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

HRID 409959
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HRID 409959 반응식
C(OC(=O)[N:7]([CH2:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[S:27][C:26]3[C:21](=[N:22][CH:23]=[CH:24][C:25]=3[O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([P:45]([CH3:48])([CH3:47])=[O:46])[CH:40]=4)=[O:37])=[CH:31][C:30]=3[F:49])[CH:20]=2)=[CH:17][CH:18]=1)[CH2:8][CH2:9][O:10][CH3:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:48][P:45]([C:41]1[CH:40]=[C:39]([NH:38][C:36]([NH:35][C:32]2[CH:33]=[CH:34][C:29]([O:28][C:25]3[CH:24]=[CH:23][N:22]=[C:21]4[CH:20]=[C:19]([C:16]5[CH:17]=[CH:18][C:13]([CH2:12][NH:7][CH2:8][CH2:9][O:10][CH3:11])=[CH:14][N:15]=5)[S:27][C:26]=34)=[C:30]([F:49])[CH:31]=2)=[O:37])[CH:44]=[CH:43][CH:42]=1)([CH3:47])=[O:46]
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반응물 2

HCID 6422Trifluoroacetic acidHCID 67049417Tert-butyl(6-(7-(4-(3-(3-(dimethylphosphoryl)phenyl)ureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl(2-methoxyethyl)carbamate

생성물 1

HCID 670482601-(3-(Dimethylphosphoryl)phenyl)-3-(3-fluoro-4-(2-(5-((2-methoxyethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea수율 38.1%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

To a solution of compound 288 (230 mg, 0.32 mmol) in dichloromethane (7 mL) under nitrogen at room temperature was added trifluoroacetic acid (2.5 mL, 32 mmol). The reaction mixture was stirred for 16 h at room temperature. The solvent was removed under reduced pressure and a saturated aqueous solution of sodium bicarbonate was added. The aqueous phase was extracted with ethyl acetate (3×), the combined organic layers were concentrated. The residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; 25M column) to afford compound 289 as an off-white solid (75.3 mg, 0.122 mmol, 38.0%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.15 (s, 1H), 9.06 (s, 1H), 8.57 (d, J=1.6 Hz, 1H), 8.53 (d, J=5.6 Hz, 1H), 8.31 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 7.92-7.83 (m, 2H), 7.76 (dd, J=13.2, 2.4 Hz, 1H), 7.67-7.62 (m, 1H), 7.49-7.42 (m, 2H), 7.41-7.33 (m, 1H), 7.32-7.26 (m, 1H), 6.67 (d, J=5.6 Hz, 1H), 3.78 (s, 2H), 3.54-3.34 (2H, hidden under water signal), 3.24 (s, 3H), 2.65 (t, J=5.6 Hz, 2H), 1.65 (d, J=13.2 Hz, 6H). MS (m/z): 620.4 (M+H).

후처리

  1. customThe solvent was removed under reduced pressure
  2. additiona saturated aqueous solution of sodium bicarbonate was added
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×)
  4. concentrationthe combined organic layers were concentrated
  5. customThe residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; 25M column)

출처 및 근거

ORD 기록
ord-60676b84c26e497895503bcdf9812077
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08759522B2

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