Water → 1-[(4-Bromo-2-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 41305

反応式

HRID 41305 の反応式
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Br:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27](O)=[O:28])[CH:22]=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.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27]([N:15]2[CH2:16][CH2:17][N:12]([S:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:19])=[CH:8][CH:7]=3)(=[O:10])=[O:11])[CH2:13][CH2:14]2)=[O:28])[CH:22]=1

参加物

8

反応物 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7351504-Bromopyridine-2-carboxylic acidHCID 25545781-[4-(Trifluoromethyl)benzenesulfonyl]piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 446121931-[(4-Bromo-2-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine収率 52.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (200 mg, 0.680 mmol) in DMF (10 ml) was added 4-bromo-2-pyridinecarboxylic acid (137 mg, 0.680 mmol), HOBT.H2O (104 mg, 0.680 mmol), HBTU (258 mg, 0.680 mmol) and DIPEA (0.356 ml, 2.039 mmol) and the reaction mixture was stirred at room temperature for 2.5 hours. The DMF was evaporated under vacuo then 10 ml of DCM were added and washed with 2M aq. HCl solution (10 ml) saturated aq. NaHCO3 solution (10 ml) and brine (10 ml), dried on a phase separation cartridge and evaporated in vacuo. The crude material was purified by silica chromatography using a gradient isohexane/EtOAc [100/0] to [50/50] then to [0/100]). The desired fractions were then collected and concentrated to dryness to give 1-[(4-bromo-2-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (171 mg, 0.358 mmol, 52.6% yield).

後処理

  1. customThe DMF was evaporated under vacuo
  2. addition10 ml of DCM were added
  3. washwashed with 2M aq. HCl solution (10 ml) saturated aq. NaHCO3 solution (10 ml) and brine (10 ml)
  4. customdried on a phase separation cartridge
  5. customevaporated in vacuo
  6. customThe crude material was purified by silica chromatography
  7. customThe desired fractions were then collected
  8. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-7612fb4c33464b6db892b2754510c064
出典データセット
uspto-grants-2013_09
特許番号
US08530478B2

関連ノート

読み込み中…