Triethylamine → 3'-Pyridin-4-ylethynyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide

HRID 907572노트

반응식

HRID 907572 반응식
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27](Cl)=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.[C:32]([C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1)#[CH:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([C:33]#[C:32][C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 162169314-Ethynylpyridine hydrochlorideHCID 59013946HCID 59013946, 화합물

생성물 1

HCID 590139503'-Pyridin-4-ylethynyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매2회

반응 조건

온도
80 °C

실험 절차

3′-Chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide (200 mg, 0.441 mmol, prepared in Example 16b) was dissolved in 1.8 mL of acetonitrile. Another mixture was prepared containing 4-ethynylpyridine hydrochloride (125 mg, 0.896 mmol), palladium(II) acetate (12 mg, 0.053 mmol), copper(I) iodide (5 mg, 0.026 mmol), triphenylphosphine (28 mg, 0.107 mmol) and triethylamine (600 μL) in 600 μL of acetonitrile. The two mixtures were combined and stirred at 80° C. for 1 hr under a nitrogen atmosphere. The reaction mixture was filtered through Celite and concentrated under vacuum. The material was used without further purification.

후처리

  1. customAnother mixture was prepared
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated under vacuum
  4. customThe material was used without further purification

출처 및 근거

ORD 기록
ord-3099bd554cd6430185b1ce20fb0a5570
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013156B2

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