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2-Amino-5-methylpyridine → N,N-Dimethyl-3-[(2-methyl-6-{[(5-methylpyridin-2-yl)amino]-carbonyl}-1-benzofuran-4-yl)oxy]azetidine-1-carboxamide

HRID 1177295
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1177295
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Al](Cl)(C)C.[CH3:13][N:14]([CH3:37])[C:15]([N:17]1[CH2:20][CH:19]([O:21][C:22]2[C:27]3[CH:28]=[C:29]([CH3:31])[O:30][C:26]=3[CH:25]=[C:24]([C:32](OCC)=[O:33])[CH:23]=2)[CH2:18]1)=[O:16]>ClCCl>[CH3:37][N:14]([CH3:13])[C:15]([N:17]1[CH2:20][CH:19]([O:21][C:22]2[C:27]3[CH:28]=[C:29]([CH3:31])[O:30][C:26]=3[CH:25]=[C:24]([C:32]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=3)=[O:33])[CH:23]=2)[CH2:18]1)=[O:16]
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Komponenten

5

Edukt 3

HCID 153482-Amino-5-methylpyridineHCID 79147ChlorodimethylaluminumHCID 59560208Ethyl 4-({1-[(dimethylamino)carbonyl]azetidin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate

Produkt 1

HCID 59559897N,N-Dimethyl-3-[(2-methyl-6-{[(5-methylpyridin-2-yl)amino]-carbonyl}-1-benzofuran-4-yl)oxy]azetidine-1-carboxamideAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-methylpyridine (203 mg, 1.88 mmol) in dichloromethane (5 mL) at 0° C. was added Al(CH3)2Cl (1.88 mL, 1M in hexanes) drop wise. After the addition, the ice-bath was removed, and the mixture was stirred for 30 minutes at room temperature. Ethyl 4-({1-[(dimethylamino)carbonyl]azetidin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate (65 mg, 0.19 mmol) was added and the stirring was continued for 14 h. The reaction was quenched with potassium sodium tartrate tetrahydrate (20% w/w) cautiously. The product was extracted with CHCl3, washed with brine and dried over Na2SO4. The product was purified by gradient silica gel chromatography using CHCl3/MeOH (95/5 to 85/15) to give the title compound (70 mg, 90%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.15 (s, 3 H) 2.37 (s, 3 H) 2.78 (s, 6 H) 3.30-3.44 (m, 2 H) 3.44-3.60 (m, 1 H) 3.88 (dd, J=12.13, 6.06 Hz, 1 H) 4.05 (dd, J=11.75, 2.40 Hz, 1 H) 6.70 (s, 1 H) 6.98 (d, J=9.60 Hz, 1 H) 7.71-7.85 (m, 1 H) 7.92 (s, 1 H) 8.17 (d, J=8.34 Hz, 1 H) 8.28-8.44 (m, 2 H); MS (ESI, pos): 409.

Aufarbeitung

  1. additionAfter the addition
  2. customthe ice-bath was removed
  3. waitthe stirring was continued for 14 h
  4. customThe reaction was quenched with potassium sodium tartrate tetrahydrate (20% w/w) cautiously
  5. extractionThe product was extracted with CHCl3
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. customThe product was purified by gradient silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0cce22e25fe74023a8f3a9df4840f335
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842713B2

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