Diethyl Ether → HCID 59471682、化合物

HRID 2204844

反応式

HRID 2204844 の反応式
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH:31]=[CH:30][C:24]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])=[CH:23][CH:22]=2)=[N:6][C:7]=1[C:8](=O)[NH:9][NH:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[N:14]=1)=[O:12].CCN(C(C)C)C(C)C.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>C(#N)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH:22]=[CH:23][C:24]([C:25]([N:27]([CH3:28])[CH3:29])=[O:26])=[CH:30][CH:31]=2)=[N:6][C:7]=1[C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[N:14]=2)=[N:10][N:9]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 70579Triphenylphosphine dibromideHCID 81531DiisopropylethylamineHCID 594722274-(5-amino-6-(2-(6-aminopyridine-2-carbonyl)hydrazinecarbonyl)pyrazin-2-yl)-N,N-dimethylbenzamide

生成物 1

HCID 59471682HCID 59471682、化合物収率 54%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a suspension of 4-[5-amino-6-[[(6-aminopyridine-2-carbonyl)amino]carbamoyl]pyrazin-2-yl]-N,N-dimethyl-benzamide (80 mg, 0.1903 mmol) in anhydrous acetonitrile (1.600 mL) cooled in an ice bath, was added DIPEA (73.78 mg, 99.43 μL, 0.5709 mmol) followed by dibromo(triphenyl)phosphorane (104.4 mg, 0.2474 mmol) portionwise. The resulting mixture was stirred at room temperature for 30 min. The precipitate was isolated by filtration, washed with small amount of acetonitrile giving a pale yellow solid. The solid was triturated in hot acetonitrile, cooled, filtered and washed acetonitrile then ether to give the pure product (36.1 mg, 54% yield); 1H NMR (400 MHz, DMSO) d 2.98-3.02 (m, 6H), 6.53 (br s, 2H), 6.69 (m, 1.5H), 7.16 (m, 0.5H), 7.16 (m, 1H), 7.53-7.66 (m, 3H), 8.11 (m, 2H) and 8.94 (s, 1H) ppm; MS (ES+) 403.29

後処理

  1. temperaturecooled in an ice bath
  2. customThe precipitate was isolated by filtration
  3. washwashed with small amount of acetonitrile giving a pale yellow solid
  4. customThe solid was triturated in hot acetonitrile
  5. temperaturecooled
  6. filtrationfiltered
  7. washwashed acetonitrile

出典と根拠

ORDレコード
ord-8d58237d732e4db886dc43563b06dab8
出典データセット
uspto-grants-2016_06
特許番号
US09365557B2

関連ノート

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