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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Trifluoroacetic acid → 6-(2-chloro-4-(1,3,4-oxadiazol-2-yl)phenyl)-8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 387219
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HRID 387219 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[C:35](=[O:36])[N:34]([CH2:37][CH3:38])[C:15]2[N:16]=[C:17]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)=[CH:23][CH:22]=3)[N:18]=[CH:19][C:14]=2[CH:13]=1)[C:5]([NH:7][NH2:8])=[O:6].F[C:40](F)(F)C(O)=O>C(OCC)(OCC)OCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:40]=[N:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[C:12]1[C:35](=[O:36])[N:34]([CH2:37][CH3:38])[C:15]2[N:16]=[C:17]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)=[CH:25][CH:26]=3)[N:18]=[CH:19][C:14]=2[CH:13]=1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 671196213-Chloro-4-{8-ethyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}benzoic acid hydrazide

생성물 1

HCID 513542406-(2-chloro-4-(1,3,4-oxadiazol-2-yl)phenyl)-8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one수율 50%

시약·촉매·용매 1

HCID 31214Ethyl orthoformate용매

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온도
130 °C

실험 절차

3-Chloro-4-{8-ethyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}benzoic acid hydrazide (7, 30 mg, 0.06 mmol) was suspended in triethyl orthoformate (5 mL) to which was added trifluoroacetic acid (1 mL). The resulting reaction mixture was heated at 130° C. for 2 h. The volatiles were removed and the residue was taken up in dichloromethane (1×20 mL) and washed with 10% sodium hydroxide solution (2×10 mL). The organic layer was dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography using dichloromethane:methanol (95:5). The title compound (18 mg, 0.03 mmol, 50%) was obtained as a yellow solid. ESMS m/z 543 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.57 (s, 1H) 8.50 (s, 1H) 8.21 (d, J=1.5 Hz, 1H) 8.04 (dd, J=8.0, 1.5 Hz, 1H) 7.62 (s, 1H) 7.52-7.60 (m, 3H) 7.29 (br. s., 1H) 6.98 (d, J=9.0 Hz, 2H) 4.50 (q, J=6.8 Hz, 2H) 3.16-3.27 (m, 4H) 2.56-2.65 (m, 4H) 2.37 (s, 3H) 1.39 (d, J=6.8 Hz, 3H).

후처리

  1. customThe resulting reaction mixture
  2. customThe volatiles were removed
  3. washwashed with 10% sodium hydroxide solution (2×10 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-f0ea3ee6287b470690f1e2aacb091cfe
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08372970B2

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