Triphenylphosphine dibromide → 5-Bromo-3-(5-(3-methylthiophen-2-yl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 78629

반응식

HRID 78629 반응식
[NH2:1][C:2]1[C:3]([C:9]([NH:11][NH:12][C:13]([C:15]2[S:16][CH:17]=[CH:18][C:19]=2[CH3:20])=[O:14])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:8][C:5]1[N:4]=[C:3]([C:9]2[O:14][C:13]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[CH3:20])=[N:12][N:11]=2)[C:2]([NH2:1])=[N:7][CH:6]=1

참가 물질

5

반응물 3

HCID 70579Triphenylphosphine dibromideHCID 81531DiisopropylethylamineHCID 594723013-amino-6-bromo-N'-(3-methylthiophene-2-carbonyl)pyrazine-2-carbohydrazide

생성물 1

HCID 594718295-Bromo-3-(5-(3-methylthiophen-2-yl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine수율 59.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a suspension of 3-amino-6-bromo-N′-(3-methylthiophene-2-carbonyl)pyrazine-2-carbohydrazide (7.85 g, 22.04 mmol) in anhydrous acetonitrile (117.8 mL) cooled in an ice bath was added DIPEA (8.546 g, 11.52 mL, 66.12 mmol) followed by dibromo(triphenyl)phosphorane (12.09 g, 28.65 mmol) portionwise. The resulting suspension was stirred at room temperature for 30 min and the precipitate isolated by filtration and washed with acetonitrile to give the product as a yellow solid (4.42 g, 52% yield); 1H NMR (400 MHz, DMSO) d 2.64 (s, 3H), 7.21 (d, 1H), 7.91 (3H, m) and 8.44 (s, 1H) ppm; MS (ES+) 340.04

후처리

  1. temperaturecooled in an ice bath
  2. customthe precipitate isolated by filtration
  3. washwashed with acetonitrile

출처 및 근거

ORD 기록
ord-b0660fef268f406389399a60a34a07e2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841308B2

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