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Hydrochloric Acid → Tert-butyl 2,4-dimethoxybenzyl6-amino-1-methyl-1h-imidazo[4,5-c]pyridin-4-ylcarbamate

HRID 220341
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 220341
[CH3:1][O:2][C:3]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:4]=1[CH2:5][N:6]([C:14]1[C:19]2[N:20]=[CH:21][N:22]([CH3:23])[C:18]=2[CH:17]=[C:16]([N:24]=C(C2C=CC=CC=2)C2C=CC=CC=2)[N:15]=1)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].Cl>C1COCC1>[NH2:24][C:16]1[N:15]=[C:14]([N:6]([CH2:5][C:4]2[CH:38]=[CH:39][C:40]([O:42][CH3:43])=[CH:41][C:3]=2[O:2][CH3:1])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:19]2[N:20]=[CH:21][N:22]([CH3:23])[C:18]=2[CH:17]=1
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 58180611tert-butyl 2,4-dimethoxybenzyl(6-(diphenylmethyleneamino)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)carbamate

Produkt 1

HCID 58180570Tert-butyl 2,4-dimethoxybenzyl6-amino-1-methyl-1h-imidazo[4,5-c]pyridin-4-ylcarbamateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 1000 mL round bottom flask, tert-butyl 2,4-dimethoxybenzyl(6-(diphenylmethyleneamino)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)carbamate (example 1C, 9.2 g, 15.93 mmol) was stirred in THF (50 mL). 1 N HCl (33 mL) was added. After 2 min, the reaction was quenched with 1 N NaOH (65 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was dried under vacuum for 1 h and triturated with ether (4×). Isolated tert-butyl 6-amino-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(2,4-dimethoxybenzyl)carbamate (6.587 g, 15.93 mmol, 100% yield) as a cream solid. Material carried forward with no further purification.

Aufarbeitung

  1. customthe reaction was quenched with 1 N NaOH (65 mL) and ethyl acetate (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was dried under vacuum for 1 h
  7. customtriturated with ether (4×)

Quellen und Nachweise

ORD-Eintrag
ord-9eb6dc8c6b9f4cbd8c3050c4aac9435e
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08202881B2

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