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Potassium Carbonate → N-cyclopropyl-4-methyl-3-(1-(3-oxopiperazin-1-yl)phthalazin-6-yl)benzamide

HRID 2357583
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HRID 2357583 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]1)=[N:7][N:6]=[CH:5]2.[CH:19]1([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCO.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:19]1([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([N:12]3[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]3)=[N:7][N:6]=[CH:5]4)[CH:25]=2)[CH2:20][CH2:21]1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 684552784-(6-Bromophthalazin-1-yl)piperazin-2-one

생성물 1

HCID 11848245N-cyclopropyl-4-methyl-3-(1-(3-oxopiperazin-1-yl)phthalazin-6-yl)benzamide수율 84%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 20074477Dimethoxyethane ethanol용매

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온도
90 °C

실험 절차

A mixture of 4-(6-bromophthalazin-1-yl)piperazin-2-one (0.10 g, 326 μmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (98mg, 326 μmol), and tetrakis(triphenylphosphine)palladium (19 mg, 16 μmol) in 5 mL DME/EtOH (4:1) was treated with 2M potassium carbonate (488 μl, 977 μmol). The resulting mixture was warmed up to 90° C. and stirred for 1 h under nitrogen. The mixture was cooled to room temperature, and the crude product was purified via flash chromatography (silica gel) eluting with a gradient of 4% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM to give the title compound (0.11 g) as a pale yellow solid. Found MS(ES+): 402(M+H)+.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customthe crude product was purified via flash chromatography (silica gel)
  3. washeluting with a gradient of 4% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM

출처 및 근거

ORD 기록
ord-3e39f7ebe9c44c18835196d9e8bb646f
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07759337B2

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