Cesium carbonate → 3-Chloro-4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile

HRID 2037029

반응식

HRID 2037029 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 583137103-Chloro-4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile수율 33%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-0afea3ace91d40f696139dfdf22f48c7
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575177B2

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