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1,2-Cyclopropanedicarboxylic acid, trans- → trans-2-(4-(2,6-Dichlorobenzamido)pyridin-2-ylcarbamoyl)cyclopropanecarboxylic acid

HRID 449909
ノート
印刷プレビュー

反応式

HRID 449909 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[CH:5]=[CH:4][N:3]=1.[C@@H:19]1([C:25](O)=[O:26])[CH2:21][C@H:20]1[C:22]([OH:24])=[O:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:17])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:25]([C@@H:19]2[CH2:21][C@H:20]2[C:22]([OH:24])=[O:23])=[O:26])[CH:7]=1)=[O:18]
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

5

反応物 3

HCID 69504501,2-Cyclopropanedicarboxylic acid, trans-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59618313N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide

生成物 1

HCID 59617988trans-2-(4-(2,6-Dichlorobenzamido)pyridin-2-ylcarbamoyl)cyclopropanecarboxylic acid収率 67%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
70 °C

実験手順

To a solution of N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (141 mg, 0.50 mmol), trans-cyclopropane-1,2-dicarboxylic acid (325 mg, 2.5 mmol), and disiopropylethylamine (339 mg, 2.63 mmol) in dry DMF (5 mL) was added HATU (1951 mg, 2.5 mmol). The reaction mixture was heated at 70° C. for 6 hours and then quenched with sat. NH4Cl (100 mL). The mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by prep HPLC (10-50% CH3CN/H2O with 0.1% formic acid) to give trans-2-(4-(2,6-dichlorobenzamido)pyridin-2-ylcarbamoyl)cyclopropanecarboxylic acid (132 mg, 67% yield). 1H NMR (400 MHz, DMSO-d6) δ 11.14 (s, 1H), 10.86 (s, 1H), 8.38 (s, 1H), 8.23 (d, J=5.6 Hz, 1H), 7.62-7.55 (m, 2H), 7.54-7.45 (m, 2H), 1.90-1.82 (m, 1H), 1.25 (dt, J=8.0, 5.4 Hz, 3H). LCMS (ESI) m/z: 394.0 [M+H+].

後処理

  1. customquenched with sat. NH4Cl (100 mL)
  2. extractionThe mixture was extracted with EtOAc (3×100 mL)
  3. dry with materialThe combined organic extracts were dried with Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep HPLC (10-50% CH3CN/H2O with 0.1% formic acid)

出典と根拠

ORDレコード
ord-13fb0baad3b6493383d1043c18e0046a
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08486950B2

反応ノート

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