Cesium carbonate → tert-butyl (3S)-3-{[8-(aminocarbonyl)-6-phenylquinazolin-4-yl]amino}piperidine-1-carboxylate

HRID 578714

반응식

HRID 578714 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]([C:13]1[CH:14]=[C:15](I)[CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][N:19]=[C:18]2[NH:23][C@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1)=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+]>C(P([Pd]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C.C1COCC1>[NH2:10][C:11]([C:13]1[CH:14]=[C:15]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][N:19]=[C:18]2[NH:23][C@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1)=[O:12]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 66762696tert-butyl (3S)-3-{[8-(aminocarbonyl)-6-iodoquinazolin-4-yl]amino}piperidine-1-carboxylate

생성물 1

HCID 66763488tert-butyl (3S)-3-{[8-(aminocarbonyl)-6-phenylquinazolin-4-yl]amino}piperidine-1-carboxylate

시약·촉매·용매 2

HCID 178454917HCID 178454917, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

Combined phenylboronic acid (16.18 mg; 0.13 mmol; 1.20 eq.), tert-butyl (3S)-3-{[8-(aminocarbonyl)-6-iodoquinazolin-4-yl]amino}piperidine-1-carboxylate (55.00 mg; 0.11 mmol; 1.00 eq.), and bis(tri-tert-butylphosphoranyl)palladium (5.67 mg; 0.01 mmol; 0.10 eq.) in a microwave tube. Then added THF (0.70 ml) followed by cesium carbonate (0.22 ml; 2.00 M; 0.44 mmol; 4.00 eq.). Heated reaction in the microwave at 130 deg C. for 20 minutes. LCMS: M+1=448 major peak (266 present). Concentrated reaction. Purified by silica gel chromatography (Biotage; 10 g column; 15 mL/min; 1-10% MeOH/CH2Cl2). Concentrated product to give an oil. LCMS: M+1=448 major peak.

후처리

  1. temperatureHeated
  2. customreaction in the microwave at 130 deg C
  3. concentrationConcentrated
  4. customreaction
  5. customPurified by silica gel chromatography (Biotage; 10 g column; 15 mL/min; 1-10% MeOH/CH2Cl2)
  6. customConcentrated product to give an oil

출처 및 근거

ORD 기록
ord-1a53dd870e244fd2bbae339303581dfa
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040560B2

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