Diisopropylethylamine → 7-[((2S)-2-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]quinoline

HRID 2365448ノート

反応式

HRID 2365448 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=O)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:47][C@@H:48]1[NH:53][CH2:52][CH2:51][N:50]([S:54]([C:57]2[CH:62]=[CH:61][C:60]([C:63]([F:66])([F:65])[F:64])=[CH:59][CH:58]=2)(=[O:56])=[O:55])[CH2:49]1.C[C@@H]1NCCN(S(C2C=CC(OC(F)(F)F)=CC=2)(=O)=O)C1>CN(C)C=O.CC#N.CS(C)=O>[CH3:47][C@H:48]1[CH2:49][N:50]([S:54]([C:57]2[CH:58]=[CH:59][C:60]([C:63]([F:66])([F:64])[F:65])=[CH:61][CH:62]=2)(=[O:55])=[O:56])[CH2:51][CH2:52][N:53]1[C:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][CH:2]=[N:1]2)=[CH:6][CH:7]=1)=[O:13]

参加物

9

反応物 5

HCID 81531DiisopropylethylamineHCID 599475Quinoline-7-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59152075(3S)-3-methyl-1-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazineHCID 59152086(S)-3-Methyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperazine

生成物 1

HCID 673246367-[((2S)-2-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]quinoline

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

7-Quinolinecarboxylic acid (112 mg, 0.649 mmol) was weighed into a vial with the HATU (247 mg, 0.649 mmol), suspended in N,N-dimethylformamide (DMF) (2 ml) and treated with N,N-diisoproylethylamine (0.170 ml, 0.973 mmol). This mixture was stirred about 15 mins at ambient temperature. (3S)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared in a similar manner as described in Intermediate 14; 100 mg, 0.324 mmol) was then added and stirring was continued. Stirring was stopped and the reaction mixture was left to stand overnight. The mixture was partitioned between DCM and sat aq. NaHCO3 solution (10 ml each). The layers were separated (hydrophobic frit) and the aqueous was washed with further DCM (2×5 ml). The combined organic layers were concentrated to leave an orange gum (still contained DMF). This was diluted with a mixture of MeCN and DMSO to give ˜1.8 ml orange solution which was purified by MDAP as two injections. The product fractions from the two runs were combined and concentrated to give the title compound as a colourless solid (119 mg).

後処理

  1. addition100 mg, 0.324 mmol) was then added
  2. stirringstirring
  3. stirringStirring
  4. waitthe reaction mixture was left
  5. waitto stand overnight
  6. customThe mixture was partitioned between DCM
  7. customThe layers were separated (hydrophobic frit)
  8. washthe aqueous was washed with further DCM (2×5 ml)
  9. concentrationThe combined organic layers were concentrated
  10. customto leave an orange gum (still contained DMF)

出典と根拠

ORDレコード
ord-6211a7a36ba04f3fb81c440bd9ca889d
出典データセット
uspto-grants-2014_04
特許番号
US08697703B2

反応ノート

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