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Sodium Carbonate → 2-(trans)-{3'-[3-(Morpholin-4-ylcarbonyl)-4-oxo-1,8-naphthyridin-1(4H)-yl]-1,1'-biphenyl-4-yl}cyclopropanecarboxylic Acid

HRID 1294383
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인쇄 미리보기

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HRID 1294383 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:17][CH:16]3[C:18]([O:20]CC)=[O:19])=[CH:11][CH:10]=2)O1.Br[C:25]1[CH:26]=[C:27]([N:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][N:39]=3)[C:34](=[O:41])[C:33]([C:42]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[O:43])=[CH:32]2)[CH:28]=[CH:29][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:44]1([C:42]([C:33]2[C:34](=[O:41])[C:35]3[C:40](=[N:39][CH:38]=[CH:37][CH:36]=3)[N:31]([C:27]3[CH:26]=[C:25]([C:9]4[CH:10]=[CH:11][C:12]([C@@H:15]5[CH2:17][C@H:16]5[C:18]([OH:20])=[O:19])=[CH:13][CH:14]=4)[CH:30]=[CH:29][CH:28]=3)[CH:32]=2)=[O:43])[CH2:45][CH2:46][O:47][CH2:48][CH2:49]1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 66579675Ethyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxylateHCID 691580421-(3-Bromophenyl)-3-(morpholin-4-ylcarbonyl)-1,8-naphthyridin-4(1H)-one

생성물 1

HCID 103456752-(trans)-{3'-[3-(Morpholin-4-ylcarbonyl)-4-oxo-1,8-naphthyridin-1(4H)-yl]-1,1'-biphenyl-4-yl}cyclopropanecarboxylic Acid

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 86598119Dimethylformamide n-propanol용매

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온도
80 °C

실험 절차

A mixture of acid from step 2 (1 eq), amide from step 1 (1 eq), Na2CO3 (3.5 eq.; 2M in H2O), Pd(PPh3)4 (0.15 eq.) in n-propanol-DMF (1:1, 0.1M) was stirred at 80° C. for 2 h. The mixture was cooled to rt, quenched with brine and diluted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (CHCl3:THF; 50:50), triturated in ether/acetone and then isolated by filtration to afford the title compound as a solid.

후처리

  1. temperatureThe mixture was cooled to rt
  2. customquenched with brine
  3. additiondiluted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (CHCl3:THF; 50:50)
  9. customtriturated in ether/acetone
  10. customisolated by filtration

출처 및 근거

ORD 기록
ord-d4135d0cc8024763adfd698357d0e009
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07238706B2

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