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

HRID 2204838

반응식

HRID 2204838 반응식
[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

참가 물질

6

반응물 4

HCID 70579Triphenylphosphine dibromideHCID 73098Thiophene-2-carbohydrazideHCID 81531Diisopropylethylamine3회HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-12757414f3104ed6b08e84142dbb24a8
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365557B2

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