Potassium Phosphate, Tribasic → tert-Butyl-[(1R)-2-({6-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)-1-phenylethyl]carbamate

HRID 1400014노트

반응식

HRID 1400014 반응식
[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][NH:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[C:32]([F:35])([F:34])[F:33].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][NH:10][C:11]1[CH:16]=[C:15]([C:28]2[CH:29]=[CH:30][C:31]([C:32]([F:34])([F:35])[F:33])=[C:26]([F:25])[CH:27]=2)[N:14]=[CH:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 177500503-Fluoro-4-trifluoromethyl-phenylboronic acidHCID 87214707[2-(6-Chloro-pyrimidin-4-ylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 131732139tert-Butyl-[(1R)-2-({6-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)-1-phenylethyl]carbamate수율 73%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
85 °C

실험 절차

[2-(6-Chloro-pyrimidin-4-ylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester (87 mg, 0.25 mmol), 3-fluoro-4-(trifluoromethyl)-phenyl boronic acid (57 mg, 0.28 mmol), Pd(PPh3)4 (2.9 mg, 2.5 μmol) and K3PO4 (110 mg, 0.50 mmol) were placed in a sealed tube which was evacuated and refilled with N2. 1,2-Dimethoxyethane (2 mL) and water (0.5 mL) were added to the sealed tube. The reaction mixture was stirred at 85° C. overnight. The reaction mixture was cooled to rt and was filtered through a pad of MgSO4. The pad was washed with CH2Cl2. The crude filtrate was concentrated under reduced pressure and the residue was purified via reverse phase chromatography to yield the title compound (87.0 mg, 59%).

후처리

  1. customwhich was evacuated
  2. additionrefilled with N2
  3. addition1,2-Dimethoxyethane (2 mL) and water (0.5 mL) were added to the sealed tube
  4. temperatureThe reaction mixture was cooled to rt
  5. filtrationwas filtered through a pad of MgSO4
  6. washThe pad was washed with CH2Cl2
  7. concentrationThe crude filtrate was concentrated under reduced pressure
  8. customthe residue was purified via reverse phase chromatography

출처 및 근거

ORD 기록
ord-02a22a0f1d6845ab8774ead3535a33cc
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906914B2

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