Benzyl Alcohol → Benzyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate

HRID 604051노트

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HRID 604051 반응식
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:17]=1C(O)=O)[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.O(P([N:54]=[N+]=[N-])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[CH2:57]([OH:64])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1.Cl.[O:66]1[CH2:70]CCC1>C(OCC)(=O)C.C(N(CC)CC)C>[F:35][C:32]([F:34])([F:33])[C:30]1[CH:29]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:37])[F:36])[CH:31]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:24]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:22]=[CH:21][C:17]=1[NH:54][C:70](=[O:66])[O:64][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:8]1[N:9]=[CH:10][C:11]([Br:14])=[CH:12][N:13]=1

참가 물질

8

반응물 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 123414Diphenylphosphoryl azideHCID 86626801HCID 86626801, 화합물

생성물 1

HCID 86626807Benzyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate

시약·촉매·용매 2

HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

2-{[(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoic acid (2.5 g) is dissolved in tetrahydrofuran (25 ml), and thereto are added diphenoxyphosphinylazide (1.34 ml), triethylamine (174 ml) and benzyl alcohol (1.3 ml) and the mixture is heated at 60° C. overnight with stirring. The reaction solution is cooled to room temperature, and thereto are added a 1N-hydrochloric acid and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→9:1→4:1) to give benzyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate (2.66 g). MS (m/z): 707/709 [M+H]+

후처리

  1. temperatureThe reaction solution is cooled to room temperature
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→9:1→4:1)

출처 및 근거

ORD 기록
ord-2c83f9a628a540f2a65ef43c8fe4272a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906517B2

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