o-Toluenesulfonyl chloride → 7-(3-Chloro-propylsulfanyl)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

HRID 8261

反応式

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([S:25][CH2:26][CH2:27][CH2:28]O)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.C1(C)C(S([Cl:39])(=O)=O)=CC=CC=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[Cl:39][CH2:28][CH2:27][CH2:26][S:25][C:21]1[CH:20]=[C:19]2[C:24]([C:15]([C:8]3[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:11][N:10]4[CH2:12][CH2:13][CH2:14][C:9]=34)=[CH:16][CH:17]=[N:18]2)=[CH:23][CH:22]=1

参加物

実験手順

To a solution of Preparation #21, 3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylsulfanyl]-propan-1-ol (25.0 mg, 0.062 mmol) in dry pyridine (0.1 mL) is added toluene sulfonyl chloride (60.0 mg, 0.31 mmol) and the resulting mixture stirred at room temperature for 72 h. Saturated sodium bicarbonate solution is added and the resulting solution extracted with ethyl acetate. The organic layer is washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo. Purification of the residue on SiO2 (5% to 10% methanol in dichloromethane) gives the desired product, 11.2 mg (43%). MS ES+ m/e 421.1 (M+1).

後処理

extractionthe resulting solution extracted with ethyl acetate
washThe organic layer is washed with brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue on SiO2 (5% to 10% methanol in dichloromethane)

出典と根拠

ORDレコード: ord-cb9b6c262d904ba286a664c696baaedc
出典データセット: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07087626B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

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