N-methyl-2-pyrrolidone → 2-(2-chlorobenzyl)-3-[2-(tetrahydro-pyran-4-ylamino)-pyrimidin-4-yl]-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 1455246

反応式

HRID 1455246 の反応式
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][C:5]1[C:12](=[O:13])[N:8]2[CH2:9][CH2:10][CH2:11][N:7]2[C:6]=1[C:14]1[CH:19]=[CH:18][N:17]=[C:16](S(C)(=O)=O)[N:15]=1.N[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1.C[N:36]1C(=O)CCC1>CO>[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][C:5]1[C:12](=[O:13])[N:8]2[CH2:9][CH2:10][CH2:11][N:7]2[C:6]=1[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:36][CH:33]2[CH2:32][CH2:31][O:30][CH2:29][CH2:34]2)[N:15]=1

参加物

5

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 14471248Oxan-2-amineHCID 574380742-(2-chlorobenzyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

生成物 1

HCID 114417002-(2-chlorobenzyl)-3-[2-(tetrahydro-pyran-4-ylamino)-pyrimidin-4-yl]-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one収率 40%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of 2-(2-chloro-benzyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 8, (0.10, 0.26 mmol) in NMP (2 mL) is added amino tetrahydropyran (0.09 mL, 0.78 mmol). After stirring 1.5 hours at 90° C., the reaction mixture is diluted with methanol (to 5 mL) and is purified by reversed phase liquid chromatography (CH3CN/water/1% TFA) to afford 44 mg (40%) of the desired product. 1H NMR (300 MHz, CDCl3) δ 8.30 (d, J=5.1 Hz, 1H), 7.39-7.12 (m, 4H), 6.57 (d, J=5.1 Hz, 1H), 4.10-3.94 (m, 9H), 3.60-3.48 (m, 2H), 2.80-2.68 (m, 2H), 2.95-1.95 (m, 2H), 1.65-1.50 (m, 2H); ESI− MS: m/z (rel intensity) 426.0 (100, M+−H).

後処理

  1. customis purified by reversed phase liquid chromatography (CH3CN/water/1% TFA)

出典と根拠

ORDレコード
ord-fe7085b51a444e5ba2eeca0845c5ceb5
出典データセット
uspto-grants-2009_01
特許番号
US07482356B2

関連ノート

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