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Potassium Phosphate, Tribasic → 2-{(2-Methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinic acid

HRID 1944573
ノート
印刷プレビュー

反応式

HRID 1944573 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]([CH3:16])[S:12]([CH3:15])(=[O:14])=[O:13])[N:10]=1)[C:5]([OH:7])=[O:6].Cl.[CH3:18][O:19][CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]1[CH2:26][C@H:25]1[CH3:27].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC(N(C)C)=O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:18][O:19][CH2:20][CH2:21][N:22]([CH2:23][C@@H:24]1[CH2:26][C@H:25]1[CH3:27])[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]([CH3:16])[S:12]([CH3:15])(=[O:14])=[O:13])[N:10]=1)[C:5]([OH:7])=[O:6]
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 62657Potassium Phosphate, TribasicHCID 167483252-Chloro-6-[methyl(methylsulfonyl)amino]isonicotinic acidHCID 86616985trans (2-Methoxyethyl)[(2-methylcyclopropyl)methyl]amine hydrochloride

生成物 1

HCID 694982882-{(2-Methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinic acid

試薬・触媒・溶媒 2

HCID 178418851
HCID 178418851、化合物
触媒
HCID 31374Dimethylacetamide溶媒

反応条件

温度
110 °C

実験手順

A suspension of 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinic acid (20 g, 75.6 mmol), trans (2-methoxyethyl)[(2-methylcyclopropyl)methyl]amine hydrochloride (17.65 g, 98.2 mmol), potassium phosphate (48.12 g, 226.7 mmol) in DMA (300 mL) was degassed with argon for 10 min. Pd(PtBu3)2 (1.93 g, 3.78 mmol) was added and the reaction mixture was degassed with argon for 10 min. The reaction mixture was stirred at 110° C. for 24 hours. The reaction was cooled to rt, filtered through celite, rinsed with EtOAc, diluted with water, the pH was adjusted to 3-4 with 1N HCl, extracted with EtOAc (×3). The organic layer was washed with aq LiCl, dried over sodium sulfate and concentrated in vacuo to give 2-{(2-methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinic acid. 1H NMR (400 MHz, CDCl3) δ 7.05 (s, 1H), 7.62 (s, 1H), 3.76 (t, J=6.3 Hz, 2H), 3.60 (t, J=6.3 Hz, 2H), 3.52-3.43 (m, 1H), 3.39 (s, 3H), 3.36 (s, 3H), 3.38-3.30 (m, 1H), 3.18 (s, 3H), 1.23 (d, J=6.1 Hz, 3H), 0.82-0.64 (m, 2H), 0.46-0.39 (m, 1H), 0.32-0.25 (m, 1H).

後処理

  1. customwas degassed with argon for 10 min
  2. customthe reaction mixture was degassed with argon for 10 min
  3. temperatureThe reaction was cooled to rt
  4. filtrationfiltered through celite
  5. washrinsed with EtOAc
  6. additiondiluted with water
  7. extractionextracted with EtOAc (×3)
  8. washThe organic layer was washed with aq LiCl
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0451064183eb489cbd137ccbe32d1122
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08394837B2

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