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

HRID 43397

反応式

HRID 43397 の反応式
Cl.[CH3:2][C@H:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10].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.[CH3:57][C:58]1[N:63]=[CH:62][C:61]([C:64]([OH:66])=[O:65])=[CH:60][CH:59]=1.CCN(C(C)C)C(C)C>C1COCC1>[CH:64]([OH:66])=[O:65].[CH3:2][C@H:3]1[CH2:8][N:7]([C:64]([C:61]2[CH:62]=[N:63][C:58]([CH3:57])=[CH:59][CH:60]=2)=[O:65])[CH2:6][CH2:5][N:4]1[S:9]([C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=1)(=[O:11])=[O:10]

参加物

8

反応物 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66649356(2S)-2-Methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride

生成物 1

HCID 67028561(2S)-2-Methyl-4-[(6-methyl-3-pyridinyl)carbonyl]-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine formic acid salt収率 142.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2S)-2-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride (Description 8) (100 mg, 0.270 mmol) in THF (5 ml) was added HOBT.H2O (41.3 mg, 0.270 mmol), HBTU (102 mg, 0.270 mmol) and 6-methyl-3-pyridinecarboxylic acid (40.7 mg, 0.297 mmol). The mixture was stirred for 5 min before addition of DIPEA (0.118 ml, 0.674 mmol) and the resultant solution stirred at room temperature for 16 h. The mixture was then concentrated and the residue partitioned between DCM (10 ml) and water (10 ml), the layers were separated using a hydrophobic frit, the organic layers were then concentrated to dryness and the crude material dissolved in DMSO and purified by MDAP giving the title compound (100.2 mg) as a colourless oil which solidified on standing.

後処理

  1. concentrationThe mixture was then concentrated
  2. customthe residue partitioned between DCM (10 ml) and water (10 ml)
  3. customthe layers were separated
  4. concentrationthe organic layers were then concentrated to dryness
  5. dissolutionthe crude material dissolved in DMSO
  6. custompurified by MDAP

出典と根拠

ORDレコード
ord-f089adb1c31b4ba5b35f751b47bd6d2a
出典データセット
uspto-grants-2013_09
特許番号
US08536183B2

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