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Sodium Carbonate → N-Cyclopropyl-6-methyl-7-(1-((S)-3-methylmorpholino)phthalazin-6-yl)benzo[d]isoxazol-3-amine

HRID 2357545
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HRID 2357545 반응식
[CH3:1][C@@H:2]1[N:7]([C:8]2[C:17]3[C:12](=[CH:13][C:14](B(O)O)=[CH:15][CH:16]=3)[CH:11]=[N:10][N:9]=2)[CH2:6][CH2:5][O:4][CH2:3]1.[CH:21]1([NH:24][C:25]2[C:29]3[CH:30]=[CH:31][C:32]([CH3:35])=[C:33](I)[C:28]=3[O:27][N:26]=2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.CCOC(C)=O.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>[CH:21]1([NH:24][C:25]2[C:29]3[CH:30]=[CH:31][C:32]([CH3:35])=[C:33]([C:14]4[CH:13]=[C:12]5[C:17](=[CH:16][CH:15]=4)[C:8]([N:7]4[CH2:6][CH2:5][O:4][CH2:3][C@@H:2]4[CH3:1])=[N:9][N:10]=[CH:11]5)[C:28]=3[O:27][N:26]=2)[CH2:23][CH2:22]1
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 58702151N-cyclopropyl-7-iodo-6-methylbenzo[d]isoxazol-3-amineHCID 68455585(S)-1-(3-methylmorpholino)phthalazin-6-ylboronic acid

생성물 1

HCID 44568804N-Cyclopropyl-6-methyl-7-(1-((S)-3-methylmorpholino)phthalazin-6-yl)benzo[d]isoxazol-3-amine

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
130 °C

실험 절차

A mixture of (S)-1-(3-methylmorpholino)phthalazin-6-ylboronic acid (0.11 g, 0.41 mmol), N-cyclopropyl-7-iodo-6-methylbenzo[d]isoxazol-3-amine (0.100 g, 0.32 mmol), tetrakis(triphenylphosphine)palladium (18 mg, 0.016 mmol) in 1,4-dioxane (2.0 mL) and 2 N aqueous sodium carbonate (0.2 mL, 0.4 mmol) in a sealed glass tube was heated in a Personal Chemistry microwave at 130° C. for 20 min. The mixture was diluted with EtOAc (30 mL) and washed with saturated aqueous solution of sodium bicarbonate, and brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure. Flash chromatography on silica gel (ethyl acetate: chloroform 80:20) afforded the titled compound as a yellow solid. MS (ESI, pos.ion) m/z: 416.1 (M+1).

후처리

  1. washwashed with saturated aqueous solution of sodium bicarbonate, and brine
  2. dry with materialThe resulting organic solution was then dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-833f1f7c65c1479e907b48f5618042d8
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07759337B2

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