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Cesium carbonate → HCID 66801482, 화합물

HRID 2366312
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HRID 2366312 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:19]C(=O)OC(C)(C)C)[CH:5]=[C:6]([F:18])[C:7]=1[C:8]1[S:9][C:10]2[C:11](Cl)=[N:12][CH:13]=[CH:14][C:15]=2[N:16]=1.[CH3:27][C:28]1[N:33]=[CH:32][N:31]=[C:30]([NH2:34])[CH:29]=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.C([O-])([O-])=O.[Cs+].[Cs+]>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]>[NH2:19][C:4]1[CH:5]=[C:6]([F:18])[C:7]([C:8]2[S:9][C:10]3[C:11]([NH:34][C:30]4[CH:29]=[C:28]([CH3:27])[N:33]=[CH:32][N:31]=4)=[N:12][CH:13]=[CH:14][C:15]=3[N:16]=2)=[C:2]([Cl:1])[CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 5728526-Methylpyrimidin-4-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86669027HCID 86669027, 화합물

생성물 1

HCID 66801482HCID 66801482, 화합물수율 10.3%

시약·촉매·용매 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

A mixture of tert-butyl N-[3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluoro-phenyl]carbamate (56 mg, 0.135 mmol), 6-methylpyrimidin-4-amine (44 mg, 0.40 mmol), Pd2(dba)3 (6.2 mg, 0.00676 mmol), XantPhos (7.8 mg, 0.0135 mmol) and Cs2CO3 (88 mg, 0.27 mmol) in 1,4-Dioxane (2 mL) was heated at 150° C. in a microwave reactor for 20 min, The mixture was filtered through Celite, washed with EtOAc, concentrated. The crude product was purified by reverse phase HPLC to give the title compound (5.4 mg, 10% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 10.48 (s, 1H), 8.61 (s, 1H), 8.39 (d, J=5.6 Hz, 1H), 7.75 (d, J=5.6 Hz, 1H), 7.58 (s, 1H), 6.66 (s, 1H), 6.49 (dd, J=12.7, 2.0 Hz, 1H), 6.34 (s, 2H), 2.38 (s, 3H). LCMS (Method B): RT=3.43 min, m/z 387.0 [M+H+].

후처리

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with EtOAc
  3. concentrationconcentrated
  4. customThe crude product was purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-cebf736865644a6a9304e472251c445f
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08697708B2

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