3-(Methylcarbamoyl)benzeneboronic acid → HCID 59593137, 화합물

HRID 2262247노트

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HRID 2262247 반응식
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9](I)=[C:8]([CH3:12])[C:6]=2[N:7]=1.[CH3:19][NH:20][C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].CC1(C)C(C)(C)OB([C:40]2[CH:48]=[CH:47][CH:46]=[C:45]3[C:41]=2[CH:42]=[N:43][NH:44]3)O1>C([O-])([O-])=O.[Na+].[Na+].C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:44]1[C:45]2[C:41](=[C:40]([C:2]3[N:3]=[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[C:5]4[S:10][C:9]([C:27]5[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=5)[C:21]([NH:20][CH3:19])=[O:22])=[C:8]([CH3:12])[C:6]=4[N:7]=3)[CH:48]=[CH:47][CH:46]=2)[CH:42]=[N:43]1

참가 물질

7

반응물 3

HCID 27735243-(Methylcarbamoyl)benzeneboronic acidHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 595928802-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine

생성물 1

HCID 59593137HCID 59593137, 화합물

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매2회HCID 6342Acetonitrile용매2회HCID 10340Sodium Carbonate용매2회

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온도
150 °C

실험 절차

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine from Example 12 (0.1 g, 0.3 mmol), 3-(N-Methylaminocarbonyl)benzeneboronic acid (50 mg, 0.3 mmol), and bis(triphenylphosphine)palladium(II) dichloride (9 mg, 13 μmol) in 1 M aqueous Na2CO3 (0.5 mL) and acetonitrile (0.5 mL) were heated to 100° C. in a sealed microwave reactor for 10 min. Upon completion, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 (122 mg, 0.5 mmol), bis(triphenylphosphine)palladium(II) dichloride (9 mg, 13 μmol), 1 M aqueous Na2CO3 (1 mL), and acetonitrile (1 mL) were added into the same pot. The reaction mixture was heated to 150° C. in a sealed microwave reactor for 20 min. The mixture was extracted with EtOAc and CH2Cl2. The combined organics were concentrated to yield 358 after reverse phase HPLC purification (2 mg). MS (Q1) 485 (M)+

후처리

  1. extractionThe mixture was extracted with EtOAc and CH2Cl2
  2. concentrationThe combined organics were concentrated

출처 및 근거

ORD 기록
ord-adde83436b4240458779ef2716f72e18
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846929B2

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