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

HRID 41317

반응식

HRID 41317 반응식
[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

참가 물질

8

반응물 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)

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 1) (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 the title compound (171 mg).

후처리

  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

출처 및 근거

ORD 기록
ord-1c93b49c023848188c711506999d0e7e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530478B2

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