Dimethylacetamide → 2-(2,6-Dichlorophenyl)-4-(6-methylpyrimidin-4-ylamino)-2H-pyrazolo[4,3-c]pyridine-7-carbonitrile

HRID 626735노트

반응식

HRID 626735 반응식
Br[C:2]1[C:3]2[C:4](=[CH:16][N:17]([C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[N:18]=2)[C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11][N:10]=2)=[N:6][CH:7]=1.C[C:28]([N:30](C)C)=O>[C-]#N.[C-]#N.[Zn+2].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>[Cl:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:19]=1[N:17]1[CH:16]=[C:4]2[C:5]([NH:8][C:9]3[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11][N:10]=3)=[N:6][CH:7]=[C:2]([C:28]#[N:30])[C:3]2=[N:18]1

참가 물질

5

반응물 2

HCID 31374DimethylacetamideHCID 69671843[7-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine

생성물 1

HCID 696713182-(2,6-Dichlorophenyl)-4-(6-methylpyrimidin-4-ylamino)-2H-pyrazolo[4,3-c]pyridine-7-carbonitrile수율 17%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

실험 절차

A suspension of [7-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine (100 mg, 0.22 mmol), Zn(CN)2 (52 mg, 0.44 mmol), and Pd(PPh3)4 (25 mg, 0.022 mmol), in DMA (1.0 mL) was sealed in a microwave vial, purged with nitrogen, and irradiated in a microwave reactor at 150° C. for 30 minutes. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography (0-70% ethyl acetate in cyclohexane), to afford the title compound as an off-white solid (15 mg, 17% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.32 (br s, 1H), 9.36 (s, 1H), 8.80 (d, J=1.0 Hz, 1H), 8.61 (s, 1H), 8.46 (s, 1H), 7.86 (d, J=1.0 Hz, 1H), 7.83 (s, 1H), 7.74 (dd, J=7.4, 1.8 Hz, 1H), 2.50 (s, 3H). LCMS (Method B): RT=3.84 min, m/z: 396 [M+H+].

후처리

  1. custompurged with nitrogen
  2. customirradiated in a microwave reactor at 150° C. for 30 minutes
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was purified by silica gel flash chromatography (0-70% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-4dceda6478fd4012baf05d02a5aacc49
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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