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Triethylamine → 1-(2-((2,5-Dichloropyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide

HRID 592376
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HRID 592376 반응식
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:12]([NH2:14])=[O:13])[CH2:11][CH2:10]1)#[CH:2].[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([Cl:23])=[CH:18][N:17]=1.CCN(CC)CC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:15][C:16]1[N:21]=[C:20]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2([C:12]([NH2:14])=[O:13])[CH2:11][CH2:10]2)[C:19]([Cl:23])=[CH:18][N:17]=1
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 867122761-(2-Ethynylphenyl)cyclopropanecarboxamide

생성물 1

HCID 867122941-(2-((2,5-Dichloropyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

PdCl2(PPh3)2 (16 mg, 0.023 mmol) was added to a stirred solution of 1-(2-ethynylphenyl)cyclopropanecarboxamide (K6) (0.420 g, 2.26 mmol), 2,4,5-trichloropyrimidine (0.338 mL, 2.94 mmol), Et3N (1.26 mL, 9.07 mmol) and copper(I) iodide (8.6 mg, 0.045 mmol) in 1,4-dioxane (4.5 mL). The resulting mixture was stirred at 60° C. for 2.5 hours under a nitrogen atmosphere before being diluted with petroleum benzine 40-60° C. (25 mL). The resultant precipitate was filtered, dried, washed with water (50 mL) and dried to give the title compound A13 as light coloured tan solid (0.570 g, 75%); 1H NMR (300 MHz, d6-DMSO) δ 9.01 (s, 1H), 7.72 (d, J=7.1 Hz, 1H), 7.41-7.57 (m, 3H), 6.97 (brs, 1H), 6.20 (brs, 1H), 1.53 (dq, J=4.0 Hz, 2H) 1.06 (dq, J=3.7 Hz, 2H). LCMS-B: rt 6.593 min; m/z 332 [M+H]+.

후처리

  1. filtrationThe resultant precipitate was filtered
  2. customdried
  3. washwashed with water (50 mL)
  4. customdried

출처 및 근거

ORD 기록
ord-a999d0892f80493cba8258bb57107222
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238644B2

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