Nitrogen → N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine

HRID 1258562노트

반응식

HRID 1258562 반응식
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([N:17]2[C:21]([CH3:22])=[N:20][N:19]=[N:18]2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1.N#N.[CH:25]1([C:28]#[CH:29])[CH2:27][CH2:26]1.C(N(CC)CC)C>C1COCC1.CCOC(C)=O.[Cu](I)I.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>[CH:25]1([C:28]#[C:29][C:2]2[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([N:17]3[C:21]([CH3:22])=[N:20][N:19]=[N:18]3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:6]=2)[CH2:27][CH2:26]1

참가 물질

9

반응물 4

HCID 947NitrogenHCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 86653111N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine

생성물 1

HCID 86653118N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine수율 56.2%

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine (0.2 g, 0.527 mmol, 1 eq.) in 3 ml dry THF “degassed” with N2, was added cyclopropylacetylene (0.069 g, 1.05 mmol, 2 eq.) followed by triethylamine (0.213 g, 2.1 mmol, 4 eq.), Copper Iodide (0.015 g, 0.079 mmol, 0.15 eq.) and Tetrakis(triphenylphosphine)palladium (0.030 g, 0.026 mmol, 0.05 eq.). The reaction was stirred for 20 hrs at room temperature for complete conversion. The reaction was diluted with EtOAc (50 ml), filtered through “Chem Elut” cartridge, washed with fresh EtOAc (2×20 ml) and the filtrate was concentrated. The residue was chromatographed on silica gel to give N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine (0.108 g, 56% yield) as a brown gum.

후처리

  1. filtrationfiltered through “Chem Elut” cartridge
  2. washwashed with fresh EtOAc (2×20 ml)
  3. concentrationthe filtrate was concentrated
  4. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-2b3c0044b8b145dea9beee4587a1c898
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466176B2

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