Sodium Carbonate → ethyl 1-({3'-[3-[(cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]biphenyl-4-yl}methyl)cyclobutanecarboxylate

HRID 1392722노트

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HRID 1392722 반응식
[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][C:27](C(O)=O)=[CH:26][CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.BrC1C=CC([CH2:38][C:39]2([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:42][CH2:41][CH2:40]2)=CC=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:19]=[C:20]([C:24]4[CH:25]=[CH:26][C:27]([CH2:38][C:39]5([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:42][CH2:41][CH2:40]5)=[CH:28][CH:29]=4)[CH:21]=[CH:22][CH:23]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 100254323'-[3-[(Cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]-1,1'-biphenyl-4-carboxylic AcidHCID 69158278Ethyl 1-(4-bromobenzyl)cyclobutanecarboxylate

생성물 1

HCID 69158192ethyl 1-({3'-[3-[(cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]biphenyl-4-yl}methyl)cyclobutanecarboxylate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 86598119Dimethylformamide n-propanol용매

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온도
70 °C

실험 절차

A mixture of NAPHTHYRIDNONE 3 (1.0 eq), ester from step 1 (1.5 eq), Na2CO3 (3.5eq; 2M in H2O), Pd(OAc)2 (0.05eq.) and PPh3 (0.15eq.) or PdCl2dppf (0.05 eq) in n-propanol-DMF (1:1, 0.1M) was stirred at 70° C. for 2 h. The mixture was cooled to rt, quenched with AcOH and diluted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (CH2Cl2/MeOH, 99:1) afforded the title compound.

후처리

  1. temperatureThe mixture was cooled to rt
  2. customquenched with AcOH
  3. additiondiluted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eaaad3d4f83545049907e56012a1cf8a
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342024B2

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