Water → (2R)-2-methyl-1-[(6-methyl-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine formic acid salt

HRID 2066133노트

반응식

HRID 2066133 반응식
[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.[CH3:21][C:22]1[N:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][CH:23]=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>[CH:28]([OH:30])=[O:29].[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:28]([C:25]1[CH:26]=[N:27][C:22]([CH3:21])=[CH:23][CH:24]=1)=[O:29]

참가 물질

8

반응물 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59152114(3R)-3-Methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

생성물 1

HCID 67028470(2R)-2-methyl-1-[(6-methyl-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine formic acid salt수율 151.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (3R)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 12) (80 mg, 0.259 mmol) in DMF (4 ml) was added 6-methyl-3-pyridinecarboxylic acid (35.6 mg, 0.259 mmol), HOBT.H2O (39.7 mg, 0.259 mmol), HBTU (98 mg, 0.259 mmol) and DIPEA (0.136 ml, 0.778 mmol) and the reaction mixture was stirred at room temperature for 1 h. The DMF was evaporated in vacuo then 5 ml of DCM were added and washed with saturated NaHCO3 solution (5 ml), dried on a phase separation cartridge and evaporated in vacuo. The crude material was dissolved in MeCN/DMSO 1:1 and purified by MDAP to give the title compound (93 mg).

후처리

  1. customThe DMF was evaporated in vacuo
  2. addition5 ml of DCM were added
  3. washwashed with saturated NaHCO3 solution (5 ml)
  4. customdried on a phase separation cartridge
  5. customevaporated in vacuo
  6. dissolutionThe crude material was dissolved in MeCN/DMSO 1:1
  7. custompurified by MDAP

출처 및 근거

ORD 기록
ord-37726dd72fdd45689149c54e8b3f21cc
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288388B2

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