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Dimethylformamide → HCID 11749692, 화합물

HRID 2216312
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HRID 2216312 반응식
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].[CH3:40][N:41](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:40]#[N:41])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1
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참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 86595018HCID 86595018, 화합물

생성물 1

HCID 11749692HCID 11749692, 화합물수율 97%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매
HCID 178418397
HCID 178418397, 화합물
촉매

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온도
80 °C

실험 절차

A mixture of trifluoromethanesulfonic acid 4-[2-methyl-4-(2,4,6-trimethylphenylamino)-pyrimidine-5-sulfonyl]-phenyl ester (146 mg, 0.283 mmol), zinc cyanide (66 mg, 0.57 mmol), and DMF (2 mL) was degassed with N2 for 10 min, and then Pd(PPh3)4 (16 mg, 0.014 mmol) was added. The mixture was stirred at 80° C. under N2 for 2 h and then cooled to room temperature. The reaction mixture was treated with saturated aqueous NaHCO3, and extracted (3×) with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc) to provide the target compound (108 mg, 97%) as a white solid: mp 258–260° C.; 1H NMR (500 MHz, CDCl3) δ 8.76 (s, 1H), 8.21 (br s, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.84 (d, J=8.6 Hz, 2H), 6.92 (s, 2H), 2.40 (s, 3H), 2.31 (s, 3H), 2.00 (s, 6H); ESI MS m/z 393 [(M+H)+, calcd for C21H21N4O2S, 393.1].

후처리

  1. customwas degassed with N2 for 10 min
  2. temperaturecooled to room temperature
  3. extractionextracted (3×) with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-069cf8aee69d4ce4b43db1ad2e107cda
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07112585B2

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