Cesium carbonate → HCID 58313710、化合物

HRID 624812

反応式

HRID 624812 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Cl:10].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:18]1[C:23]([CH3:24])=[C:22]([N:25]([CH:33]2[CH2:35][CH2:34]2)C(=O)OC(C)(C)C)[N:21]2[N:36]=[CH:37][C:38]([CH:39]=[O:40])=[C:20]2[N:19]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[Cl:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[NH:1][C:18]1[C:23]([CH3:24])=[C:22]([NH:25][CH:33]2[CH2:34][CH2:35]2)[N:21]2[N:36]=[CH:37][C:38]([CH:39]=[O:40])=[C:20]2[N:19]=1)[C:6]#[N:7]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 5198964-Amino-3-chlorobenzonitrileHCID 634876Binap, (A+-)-HCID 86652158HCID 86652158、化合物

生成物 1

HCID 58313710HCID 58313710、化合物収率 33%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 312751,4-Dioxane溶媒

実験手順

To 4-amino-3-chlorobenzonitrile (52 mg, 0.34 mmol), Cs2CO3 (130 mg, 0.4 mmol) were added to tert-butyl 5-chloro-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (100 mg, 0.29 mmol) dissolved in 1,4-dioxane (1.1 mL). Racemic BINAP (11 mg, 0.017 mmol) and palladium(II) acetate (8 mg, 0.011 mmol) were then added. The mixture was sealed and irradiated at 110° C. for 60 min in the microwave. Et2O (3 mL) was added and the solution was filtered. The filtrate was concentrated in vacuo. The crude residue was dissolved in dichloromethane (1.5 mL) and trifluoroacetic acid (1.5 mL). After stirring at room temperature for 1 hour, the solution was concentrated under a stream of air. The crude material was purified by silica gel chromatography (3% acetone/dichloromethane) to yield the product, 3-chloro-4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile (34 mg, 33% yield). LCMS (M+1=367)

後処理

  1. customThe mixture was sealed
  2. customirradiated at 110° C. for 60 min in the microwave
  3. filtrationthe solution was filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe crude residue was dissolved in dichloromethane (1.5 mL)
  6. concentrationthe solution was concentrated under a stream of air
  7. customThe crude material was purified by silica gel chromatography (3% acetone/dichloromethane)

出典と根拠

ORDレコード
ord-de8ea8eacd724bab84f5c93314a079e9
出典データセット
uspto-grants-2016_04
特許番号
US09303033B2

関連ノート

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