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Diisopropylethylamine → (S)-6-(1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylamino)pyridazine-3-carbonitrile

HRID 407998
ノート
印刷プレビュー

反応式

HRID 407998 の反応式
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=3)[CH2:9][CH2:8]2)[C:3]1=[O:24].C(N(C(C)C)C(C)C)C.Cl[C:35]1[N:40]=[N:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=1>CN(C=O)C.CCOC(C)=O>[Cl:19][C:18]1[C:13]([N:10]2[CH2:11][CH2:12][CH:7]([N:4]3[CH2:5][CH2:6][C@H:2]([NH:1][C:35]4[N:40]=[N:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=4)[C:3]3=[O:24])[CH2:8][CH2:9]2)=[N:14][CH:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:17]=1
参加物反応条件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 81531DiisopropylethylamineHCID 133828716-Chloropyridazine-3-carbonitrileHCID 67469689(S)-3-amino-1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)pyrrolidin-2-one

生成物 1

HCID 54670892(S)-6-(1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylamino)pyridazine-3-carbonitrile収率 14.6%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

To a solution of (S)-3-amino-1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)pyrrolidin-2-one (0.15 g, 0.41 mmol) in DMF (10 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.160 g, 1.24 mmol) and 6-chloropyridazine-3-carbonitrile (0.173 g, 1.24 mmol) and the reaction was heated to 90° C. overnight. The reaction was diluted with EtOAc (150 mL) and washed with water (100 mL), and brine (10 mL), dried over MgSO4, filtered and concentrated under vacuum. The material was purified on silica, using 1:1 EtOAc:DCM as eluent to yield a solid, which was further triturated with diethyl ether to yield (S)-6-(1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylamino)pyridazine-3-carbonitrile (0.028 g, 0.060 mmol, 14% yield). Mass spectrum (apci) m/z=466.0, 467.9 (M+H).

後処理

  1. washwashed with water (100 mL), and brine (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe material was purified on silica
  6. customDCM as eluent to yield a solid, which
  7. customwas further triturated with diethyl ether

出典と根拠

ORDレコード
ord-4f49a5aec992422eb4841ff1f1d5475d
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754226B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート