Cesium carbonate → N-(6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-9-yl)-2-morpholin-4-ylacetamide

HRID 2192993노트

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HRID 2192993 반응식
Br[C:2]1[CH:25]=[CH:24][C:5]2[C:6]([NH:15][C@@H:16]([C:20]([F:23])([F:22])[F:21])[CH:17]([CH3:19])[CH3:18])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N:32]1([CH2:38][C:39]([NH2:41])=[O:40])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.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]>[CH3:18][CH:17]([CH3:19])[C@@H:16]([NH:15][C:6]1[C:5]2[CH:24]=[CH:25][C:2]([NH:41][C:39](=[O:40])[CH2:38][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:3][C:4]=2[C:13]2[C:12](=[O:14])[NH:11][CH:10]=[CH:9][C:8]=2[N:7]=1)[C:20]([F:22])([F:21])[F:23]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)2회HCID 6679102-(Morpholin-4-yl)acetamideHCID 249053779-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one

생성물 1

HCID 67415384N-(6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-9-yl)-2-morpholin-4-ylacetamide

시약·촉매·용매 2

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

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온도
100 °C

실험 절차

To a solution of 9-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one (30 mg, 0.07 mmol) in dioxane (1 mL) were added cesium carbonate (83 mg, 0.25 mmol), 2-morpholin-4-ylacetamide (10 mg, 0.07 mmol), Xantphos, (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine), (8.3 mg, 0.01 mmol), and Pd2(dba)3 (6.63 mg, 7.24 μmol). The solution was degassed by bubbling nitrogen gas for 5 min and heated to 100° C. for 2 hr. The solution was filtered and purified using reverse phase chromatography 100% H2O to 100% MeCN. LRMS (ESI) calc'd for (C23H27F3N5O3) [M+H]+, 478.2; found 478.1.

후처리

  1. customThe solution was degassed
  2. customby bubbling nitrogen gas for 5 min
  3. filtrationThe solution was filtered
  4. custompurified

출처 및 근거

ORD 기록
ord-fee94807061a4aa5b4b25dc6c83d96be
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329722B2

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