Diisopropylethylamine → 4-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]piperazine-2,6-dione

HRID 63853ノート

反応式

HRID 63853 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:30]([F:33])([F:32])[F:31])[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[C:19]([C:26]([F:29])([F:28])[F:27])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:67]1[C:72](=[O:73])[CH2:71][NH:70][CH2:69][C:68]1=[O:74]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:30]([F:32])([F:31])[F:33])[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([N:70]4[CH2:71][C:72](=[O:73])[NH:67][C:68](=[O:74])[CH2:69]4)=[O:22])=[C:19]([C:26]([F:28])([F:29])[F:27])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 338690Piperazine-2,6-dioneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1180467214-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)benzoic acid

生成物 1

HCID 1180467104-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]piperazine-2,6-dione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

Into a 25-mL round-bottom flask, was placed 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)benzoic acid (70 mg, 0.14 mmol, 1.00 equiv), N,N-dimethylformamide (3 mL), HATU (105 mg, 0.28 mmol, 2.00 equiv), DIEA (36 mg, 0.28 mmol, 1.96 equiv), piperazine-2,6-dione (32 mg, 0.28 mmol, 1.99 equiv). The resulting solution was stirred for 1 h at 25° C. The reaction was then quenched by the addition of 10 ml of water. The resulting solution was extracted with 2×10 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×20 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a TLC plate with ethyl acetate/petroleum ether (1/1). This resulted in 70 mg (76%) of 4-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]piperazine-2,6-dione as colorless oil.

後処理

  1. customInto a 25-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 10 ml of water
  3. extractionThe resulting solution was extracted with 2×10 mL of ethyl acetate
  4. washThe resulting mixture was washed with 3×20 mL of brine
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 70 mg (76%) of 4-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]piperazine-2,6-dione as colorless oil

出典と根拠

ORDレコード
ord-0fe25ff6fc2542658b272d6896f81079
出典データセット
uspto-grants-2016_09
特許番号
US09447084B2

反応ノート

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