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Dimethyl Sulfoxide → HCID 44820187, 화합물

HRID 2273991
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HRID 2273991 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=2[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:12])=[CH:4][CH:3]=1.[NH2:25][C:26]1[N:31]=[C:30](Cl)[CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>CCOC(C)=O>[NH2:25][C:26]1[N:31]=[C:30]([O:20][C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]=3[NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:15][CH:16]=2)[CH:29]=[CH:28][N:27]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 679Dimethyl Sulfoxide2회HCID 10796Cesium carbonateHCID 2233322-Amino-4-chloropyrimidineHCID 58533483HCID 58533483, 화합물

생성물 1

HCID 44820187HCID 44820187, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
150 °C

실험 절차

A mixture of 2-(4-fluorophenylamino)-N-(4-hydroxyphenyl)benzamide (157 mg, 486 μmol), 2-amino-4-chloropyrimidine (60 mg, 463 μmol), and cesium carbonate (302 mg, 926 μmol) in DMSO (2316 μl, 463 μmol) was placed in a microwave pressure vial, the vial was sealed, and the vial (reaction mixture) was heated in a Biotage Microwave to 150° C. for 12 minutes. LCMS analysis indicated that the reaction was complete. Reaction was diluted with EtOAc and washed with sat NaHCO3 (aq). The organic layer was dried over sodium sulfate and concentrated in vacuo to give a brown color oil. The oil was taken up in minimal amount of DMSO and purified by Gilson HPLC {10-80% (0.1% TFA in CH3CN) in H2O over 20 min} to afford pure N-(4-(2-aminopyrimidin-4-yloxy)phenyl)-2-(4-fluorophenylamino)benzamide. MS Calcd for C23H18FN5O2=415. Found: [M+H]+=416.

후처리

  1. customthe vial was sealed
  2. customthe vial (reaction mixture)
  3. customReaction
  4. washwashed
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a brown color oil
  8. custompurified by Gilson HPLC {10-80% (0.1% TFA in CH3CN) in H2O over 20 min}

출처 및 근거

ORD 기록
ord-392fd6c3e4fd4a1da568c99fd9426fbb
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09126935B2

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