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N-methyl-2-pyrrolidone → (1S,2S)-N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide

HRID 1409275
ノート
印刷プレビュー

反応式

HRID 1409275 の反応式
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:13]([C@H:15]2[CH2:17][C@@H:16]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:14])[CH:3]=1.Cl.[NH:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:32](N)=[O:33])[CH2:27][CH2:26]1.[CH3:35]N1C(=O)CCC1>CS(C)=O.CO>[C:32]([NH:31][CH:28]1[CH2:29][CH2:30][N:25]([C:2]2[N:7]3[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]3[N:5]=[C:4]([NH:12][C:13]([C@H:15]3[CH2:17][C@@H:16]3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:14])[CH:3]=2)[CH2:26][CH2:27]1)(=[O:33])[CH3:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 17750380(Piperidin-4-yl)urea hydrochlorideHCID 86652283(1S,2S)-N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide

生成物 1

HCID 67064683(1S,2S)-N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide収率 59%

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
触媒
HCID 887Methanol溶媒

実験手順

The title compound was prepared by combining (1R,2R)—N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide (8E, 0.08 g, 0.245 mmol) and the 1-(piperidin-4-yl)urea hydrochloride (0.088 g, 0.490 mmol) in NMP (0.816 ml) and heating the mixture at 85° C. overnight. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by 40-60% preparatory HPLC (ACN/MeOH)/H2O+0.01% TFA). Lyophilization of the combined fractions gave 63 mg (59%) of the titled compound as a yellow solid. 1H NMR (DMSO-d6) δ: 10.95 (s, 1H), 7.24-7.35 (m, 3H), 7.14-7.24 (m, 3H), 6.08 (s, 3H), 4.24 (d, J=13.1 Hz, 2H), 3.66 (br. s., 2H), 3.17 (dd, J=23.7, 12.1 Hz, 2H), 2.39-2.47 (m, 1H), 2.26-2.38 (m, 4H), 1.90 (d, J=13.1 Hz, 2H), 1.34-1.59 (m, 4H); ESI-MS: m/z 433.0 (M+H)+.

後処理

  1. customThe title compound was prepared
  2. customwas then purified by 40-60% preparatory HPLC (ACN/MeOH)/H2O+0.01% TFA)

出典と根拠

ORDレコード
ord-81406437fbfa4f0cb34f99b8cd7415a2
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921358B2

反応ノート

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