Ethyl Acetate → {6-(2,4-Dichloro-phenyl)-3-[(tetrahydro-pyran-4-carbonyl)-amino]-imidazo[1,2-a]pyridin-7-ylmethyl}-carbamic acid tert-butyl ester

HRID 420534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420534
[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([NH2:26])=[CH:24][N:25]=[C:11]2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCN([CH:34]([CH3:36])[CH3:35])C(C)C.CN([C:40]([O:44]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCO[C:64]([CH3:66])=[O:65]>CN(C=O)C>[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([NH:26][C:40]([CH:35]3[CH2:34][CH2:36][O:65][CH2:64][CH2:66]3)=[O:44])=[CH:24][N:25]=[C:11]2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57906484[3-Amino-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 57906481{6-(2,4-Dichloro-phenyl)-3-[(tetrahydro-pyran-4-carbonyl)-amino]-imidazo[1,2-a]pyridin-7-ylmethyl}-carbamic acid tert-butyl esterAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of [3-amino-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl]-carbamic acid tert-butyl ester (100 mg, 0.25 mmol), tetrahydro-pyran-4-arboxylic acid (192 mg, 1.47 mmol) and DIPEA (0.52 mL, 2.95 mmol) in DMF (3 mL) was added HATU (560 mg, 1.47 mmol) at RT. The reaction mixture was heated at 80° C. and stirred for 24 h, then poured into AcOEt (50 mL) and washed with a 2.0 M aqueous Na2CO3 solution (2×25 mL). The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/MeOH 99:1→84:16) to yield the title compound (79.5 mg, 0.153 mmol, 62%). MS: 519 [M+1]+; HPLC: AtRet=1.49; TLC: RF 0.14 (DCM/MeOH 95:5).

Aufarbeitung

  1. washwashed with a 2.0 M aqueous Na2CO3 solution (2×25 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/MeOH 99:1→84:16)

Quellen und Nachweise

ORD-Eintrag
ord-59377f9632604eceaaf9b36c8a2b60da
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097617B2

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