Sodium Carbonate → 5-[2-(4-{1-[(Tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenylpyrimido[1,2-b]indazol-8-yl]pyrazole-1-carboxylic acid tert-butyl ester

HRID 877050노트

반응식

HRID 877050 반응식
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:30][N:21]4[N:22]=[C:23]5[C:28]([CH:27]=[CH:26][C:25](Br)=[CH:24]5)=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:39]([O:43][C:44]([N:46]1[C:50](B(O)O)=[CH:49][CH:48]=[N:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[C:39]([O:43][C:44]([N:46]1[C:50]([C:25]2[CH:26]=[CH:27][C:28]3[C:23]([CH:24]=2)=[N:22][N:21]2[CH:30]=[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:18]([C:15]4[CH:16]=[CH:17][C:12]([C:8]5([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:38])[CH2:11][CH2:10][CH2:9]5)=[CH:13][CH:14]=4)=[N:19][C:20]=32)=[CH:49][CH:48]=[N:47]1)=[O:45])([CH3:42])([CH3:40])[CH3:41]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 467389241H-Pyrazole-5-boronic acid, N1-BOC protectedHCID 86702528{1-[4-(8-Bromo-3-phenylpyrimido[1,2-b]indazol-2-yl)phenyl]-cyclobutyl}carbamic acid tert-butyl ester

생성물 1

HCID 679912345-[2-(4-{1-[(Tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenylpyrimido[1,2-b]indazol-8-yl]pyrazole-1-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 178477754HCID 178477754, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
105 °C

실험 절차

100 mg (0.18 mmol) {1-[4-(8-Bromo-3-phenylpyrimido[1,2-b]indazol-2-yl)phenyl]-cyclobutyl}carbamic acid tert-butyl ester, intermediate example Int-2-2, 74.5 mg (0.35 mmol) [1-(tert-butoxycarbonyl)-1H-pyrazol-5-yl]boronic acid, 14.3 mg (0.02 mmol) 1,1 bis(diphenylphosphino)ferrocenedichloro-palladium(II) and 55.8 mg (0.53 mmol) sodium carbonate in 1.8 mL dioxane and 0.3 mL water (both solvents had been degassed) were heated in the microwave for 30′ at 105° C. The reaction mixture was poured on water/dichloromethane/saturated ammonium chloride and vigorously stirred for 30′. The organic phase was separated, washed twice with brine, dried (sodium sulfate) and filtrated. The solvent was evaporated and the crude residue (181 mg>100%) was used in the next step without further purification.

후처리

  1. additionThe reaction mixture was poured on water/dichloromethane/saturated ammonium chloride
  2. customThe organic phase was separated
  3. washwashed twice with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltrated
  6. customThe solvent was evaporated
  7. customthe crude residue (181 mg>100%) was used in the next step without further purification

출처 및 근거

ORD 기록
ord-f78e78a895674c169e1203c6207284a3
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987286B2

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