Water → (2S)-2-Methyl-1-[(5-methyl-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 43402

反応式

HRID 43402 の反応式
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3]1.C1C=CC2N(O)N=NC=2C=1.O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:56][C:57]1[CH:58]=[C:59]([C:63](O)=[O:64])[CH:60]=[N:61][CH:62]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C@H:2]1[CH2:3][N:4]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)(=[O:9])=[O:10])[CH2:5][CH2:6][N:7]1[C:63]([C:59]1[CH:60]=[N:61][CH:62]=[C:57]([CH3:56])[CH:58]=1)=[O:64]

参加物

8

反応物 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2562085-Methylnicotinic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59152086(S)-3-Methyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperazine

生成物 1

HCID 59161391(2S)-2-Methyl-1-[(5-methyl-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (3S)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 2) (100 mg, 0.324 mmol) in DMF (5 ml) was added HOBT.H2O (49.7 mg, 0.324 mmol), HBTU (123 mg, 0.324 mmol), 5-methyl-3-pyridinecarboxylic acid (44.5 mg, 0.324 mmol) and DIPEA (0.170 ml, 0.973 mmol) and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was evaporated in vacuo. The residue was dissolved in DCM (50 ml), transferred to a separating funnel and the solution was washed with aqueous NaHCO3 (5 ml), twice. The organic layer was dried with magnesium sulphate which was removed by filtration and the filtrate evaporated to dryness in vacuo. The residual oil was dissolved in 1:1 MeCN/DMSO (1.8 ml) and purified by MDAP in two batches. The fractions containing the desired product were combined and evaporated to dryness in vacuo to the title compound (95 mg).

後処理

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in DCM (50 ml)
  3. customtransferred to a separating funnel
  4. washthe solution was washed with aqueous NaHCO3 (5 ml)
  5. dry with materialThe organic layer was dried with magnesium sulphate which
  6. customwas removed by filtration
  7. customthe filtrate evaporated to dryness in vacuo
  8. dissolutionThe residual oil was dissolved in 1:1 MeCN/DMSO (1.8 ml)
  9. custompurified by MDAP in two batches
  10. additionThe fractions containing the desired product
  11. customevaporated to dryness in vacuo to the title compound (95 mg)

出典と根拠

ORDレコード
ord-51f6b6fe6ce645498e42b49dbbb23c08
出典データセット
uspto-grants-2013_09
特許番号
US08536183B2

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