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

HRID 2204851ノート

反応式

HRID 2204851 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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

後処理

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

出典と根拠

ORDレコード
ord-697dc441f44d49d68012f698508f728d
出典データセット
uspto-grants-2016_06
特許番号
US09365557B2

反応ノート

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