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

HRID 78615

反応式

HRID 78615 の反応式
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH:19][NH2:20])=O.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCN(C(C)C)C(C)C>C(#N)C>[Br:8][C:5]1[N:4]=[C:3]([C:9]2[O:11][C:17]([C:13]3[S:12][CH:16]=[CH:15][CH:14]=3)=[N:19][N:20]=2)[C:2]([NH2:1])=[N:7][CH:6]=1

参加物

6

反応物 4

HCID 70579Triphenylphosphine dibromideHCID 73098Thiophene-2-carbohydrazideHCID 81531Diisopropylethylamine3 回HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

生成物 1

HCID 594719085-Bromo-3-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine収率 58.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

3-amino-6-bromo-pyrazine-2-carboxylic acid (3.2 g, 14.68 mmol) and thiophene-2-carbohydrazide (2.152 g, 14.68 mmol) were suspended in acetonitrile (48.00 mL) at room temperature and dibromo(triphenyl)phosphorane (24.79 g, 58.72 mmol) was added, followed byadditional acetonitrile (16.00 mL). The reaction mixture turned bright yellow in colour and was stirred at room temperature for 1 h. After this time, the reaction mixture cooled in an icebath and DIPEA (7.209 g, 9.716 mL, 55.78 mmol) was added dropwise. The reaction mixture was stirred in the ice bath for 1 h and then additional DIPEA (2.277 g, 3.069 mL, 17.62 mmol) added and the reaction mixture stirred for left for 30 mins and further DIPEA (1.897 g, 2.557 mL, 14.68 mmol) added. The reaction mixture was stirred for 1 h and then filtered. The solid was washed with ether, isolated and then triturated with acetonitrile and washed with ether to give the product as a yellow solid (2.776 g, 57% yield); 1H NMR (400.0 MHz, DMSO) 7.35 (s, 1H), 7.80 (br s, 2H), 7.98 (m, 1H), 8.04 (m, 1H) and 8.45 (s, 1H); MS (ES+) 326.04

後処理

  1. additionwas added dropwise
  2. stirringthe reaction mixture stirred
  3. waitfor left for 30 mins
  4. stirringThe reaction mixture was stirred for 1 h
  5. filtrationfiltered
  6. washThe solid was washed with ether
  7. customisolated
  8. customtriturated with acetonitrile
  9. washwashed with ether

出典と根拠

ORDレコード
ord-539a504bdf254e19943bf081b9102183
出典データセット
uspto-grants-2014_09
特許番号
US08841308B2

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