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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874477、化合物

HRID 1093839
ノート
印刷プレビュー

反応式

HRID 1093839 の反応式
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:12]=[C:13]([N:18]2[CH:22]=[C:21]([C:23]([OH:25])=O)[N:20]=[N:19]2)[CH:14]=[C:15]([F:17])[CH:16]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:48][CH2:49][C:50]([N:52]1[CH2:57][CH2:56][CH:55]([O:58][C:59]2[CH:60]=[N:61][CH:62]=[C:63]([Cl:65])[CH:64]=2)[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[Cl:65][C:63]1[CH:64]=[C:59]([O:58][CH:55]2[CH2:54][CH2:53][N:52]([C:50](=[O:51])[CH2:49][NH:48][C:23]([C:21]3[N:20]=[N:19][N:18]([C:13]4[CH:14]=[C:15]([F:17])[CH:16]=[C:11]([F:10])[CH:12]=4)[CH:22]=3)=[O:25])[CH2:57][CH2:56]2)[CH:60]=[N:61][CH:62]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 287431861-(3,5-difluorophenyl)-1H-1,2,3-triazole-4-carboxylic acidHCID 665916722-Amino-1-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-ethanone hydrochloride

生成物 1

HCID 57874477
HCID 57874477、化合物
収率 54.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (149.2 mg, 1.15 mmol) was added to a stirred solution of 1-(3,5-difluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (65 mg, 0.28 mmol) in DMF (2 mL) followed by HOBt (43 mg, 0.31 mmol) and EDCI (110 mg, 0.57 mmol). After 2 minutes of stirring, 2-amino-1-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (88.4 mg, 0.28 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and the precipitate was collected. The crude solid was purified by recrystallisation from a mixture of DCM and hexane to afford 95 mg (54.4% Yield) of 1-(3,5-difluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 477.12, 98.45%. 1H NMR (300 MHz, DMSO-d6): δ 9.5 (s, 1H), 8.5 (t, 1H), 8.3 (d, 1H), 8.2 (d, 1H), 7.9 (d, 2H), 7.75 (t, 1H), 7.58-7.5 (m, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 4.0-3.8 (m, 1H), 3.8-3.6 (m, 1H), 3.4 (m, 1H), 3.2 (m, 1H), 2.1-1.9 (m, 2H), 1.9-1.5 (m, 2H).

後処理

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customthe precipitate was collected
  4. customThe crude solid was purified by recrystallisation from a mixture of DCM and hexane

出典と根拠

ORDレコード
ord-83e300a1dc684632804cdecb1e9e8bb1
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08129376B2

反応ノート

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