Sodium Carbonate → HCID 71282814, 화합물

HRID 1752433노트

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HRID 1752433 반응식
[F:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10](B3OC(C)(C)C(C)(C)O3)=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[NH2:24][C:25](=[O:39])[C@@H:26]([NH:28][C:29]1[N:34]=[C:33](Cl)[N:32]=[C:31]([C:36]([NH2:38])=[O:37])[CH:30]=1)[CH3:27].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O.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>[NH2:24][C:25](=[O:39])[C@@H:26]([NH:28][C:29]1[N:34]=[C:33]([C:10]2[CH:9]=[N:8][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:23][CH:22]=3)=[CH:12][CH:11]=2)[N:32]=[C:31]([C:36]([NH2:38])=[O:37])[CH:30]=1)[CH3:27]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 71092939HCID 71092939, 화합물HCID 89422280HCID 89422280, 화합물

생성물 1

HCID 71282814HCID 71282814, 화합물수율 50.5%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 86587095Dimethoxyethane ethanol water용매

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온도
100 °C

실험 절차

A mixture of 2-(4-fluorophenoxy)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (158 mg, 0.5 mmol), (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide (121 mg, 0.5 mmol), Na2CO3 (2 M, 1 mL, 2 mmol) and Pd(PPh3)2Cl2 (20 mg, 0.025 mmol) in DME/EtOH/H2O (2 mL/1 mL/2 mL) was purged with Ar for one minute, then stirred at 100° C. for 14 hrs. The reaction mixture was then worked up with DCM. The DCM was isolated, dried over MgSO4, and removed under vacuum. The residue was subjected to silica gel flash chromatography using dichloromethane/methanol as the eluent to give (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(6-(4-fluorophenoxy)pyridin-3-yl)pyrimidine-4-carboxamide as a gray solid (100 mg, yield 50%). NMR (DMSO-d6): 9.3 (1H, s), 8.9 (1H, m), 8.3 (1H, s), 8.05 (1H, m), 7.75 (1H, s), 7.5 (1H, s), 7.2-7.4 (4H, m), 6.95-7.15 (2H, m), 6.80 (1H, s), 4.5 (1H, m), 1.35 (3H, d, J=7.0 Hz). LC/MS: m/z=398 [M+H]+.

후처리

  1. customwas purged with Ar for one minute
  2. customThe DCM was isolated
  3. dry with materialdried over MgSO4
  4. customremoved under vacuum

출처 및 근거

ORD 기록
ord-81fb9a18293b40be9f59adeaa28f05f4
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163008B2

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