Water → 3-[((3S)-3-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]pyrazolo[1,5-a]pyrimidine

HRID 418298ノート

反応式

HRID 418298 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.[N:57]1[N:61]2[CH:62]=[CH:63][CH:64]=[N:65][C:60]2=[C:59]([C:66](O)=[O:67])[CH:58]=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:2][C@@H:3]1[N:4]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=2)(=[O:11])=[O:10])[CH2:5][CH2:6][N:7]([C:66]([C:59]2[CH:58]=[N:57][N:61]3[CH:62]=[CH:63][CH:64]=[N:65][C:60]=23)=[O:67])[CH2:8]1

参加物

8

反応物 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic 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 591521083-[((3S)-3-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]pyrazolo[1,5-a]pyrimidine収率 69.7%

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 (may be prepared as described in Description 6) (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 pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (48.4 mg, 0.297 mmol). The mixture was stirred for 5 minutes before addition of DIPEA (0.118 ml, 0.674 mmol) and the resultant solution stirred at rt for 16 hours. 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 and the organic layers concentrated to dryness and the crude material dissolved in DMSO and purified by MDAP to give the title compound (85.3 mg) as a white solid.

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 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-eb0845f86c284cd9b0afbedca2514b98
出典データセット
uspto-grants-2012_01
特許番号
US08093249B2

反応ノート

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