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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Potassium Phosphate, Tribasic → 7-(2-Aminopyrimidin-5-yl)-1-{[(1r)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5h-pyrido[4,3-b]indole-4-carboxamide

HRID 1970996
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HRID 1970996 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([NH:15][C@H:16]([CH:21]4[CH2:23][CH2:22]4)[C:17]([F:20])([F:19])[F:18])=[N:13][CH:12]=[C:11]([C:24]([NH2:26])=[O:25])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[NH2:27][C:28]1[N:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[NH2:27][C:28]1[N:33]=[CH:32][C:31]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:14]([NH:15][C@H:16]([CH:21]5[CH2:22][CH2:23]5)[C:17]([F:19])([F:18])[F:20])=[N:13][CH:12]=[C:11]([C:24]([NH2:26])=[O:25])[C:7]=4[NH:8][C:9]=3[CH:10]=2)=[CH:30][N:29]=1
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참가 물질

7

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HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 565954477-Chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carboxamide

생성물 1

HCID 426229347-(2-Aminopyrimidin-5-yl)-1-{[(1r)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5h-pyrido[4,3-b]indole-4-carboxamide

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

7-Chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carboxamide (8.36 g, 21.8 mmol) and 2-aminopyrimidine-5-boronic acid pinacol ester (7.73 g, 34.9 mmol) were placed in a flask. Pd2(dba)3 (2.0 g, 2.184 mmol), tricyclohexylphosphine (1.53 g, 5.46 mmol), dioxane (437 ml) and K3PO4 (1.25 M in water, 59.2 ml, 74.0 mmol) were added and the flask purged with N2 for 15 min. The reaction mixture was heated at 100° C. for 4 h, and cooled to room temperature. The mixture was diluted with EtOAc, washed with water and brine, dried (magnesium sulfate), and concentrated. Flash chromatography gave the title compound as a white solid. 1H NMR (600 MHz, CD3SOCD3) δ 11.64 (s, 1H); 8.62 (s, 2H); 8.54 (d, 1H); 8.52 (s, 1H); 7.97 (br s, 1H); 7.95 (d, 1H); 7.53 (dd, 1H); 7.30 (br s, 1H); 7.01 (d, 1H); 6.79 (s, 2H); 4.87 (m, 1H); 1.62 (m, 1H); 0.76 (m, 1H); 0.64 (m, 1H); 0.55 (m, 1H); 0.35 (m, 1H). LRMS (APCI) calc'd for (C21H18F3N7O) [M+H]+, 442.2. found 442.1.

후처리

  1. customthe flask purged with N2 for 15 min
  2. temperaturecooled to room temperature
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bbd2a2d8d04a46c6a2d313663d321120
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431569B2

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