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

HRID 1944573
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HRID 1944573 반응식
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]
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6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 167483252-Chloro-6-[methyl(methylsulfonyl)amino]isonicotinic acidHCID 86616985trans (2-Methoxyethyl)[(2-methylcyclopropyl)methyl]amine hydrochloride

생성물 1

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

시약·촉매·용매 2

HCID 178418851
HCID 178418851, 화합물
촉매
HCID 31374Dimethylacetamide용매

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온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0451064183eb489cbd137ccbe32d1122
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394837B2

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