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

HRID 626735ノート

反応式

HRID 626735 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-4dceda6478fd4012baf05d02a5aacc49
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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