Trifluoroacetic acid → N-(5-amino-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 570325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570325
C(O)(C(F)(F)F)=O.[N:8]1[CH:9]=[C:10]([C:17]([NH:19][C:20]2[CH:21]=[C:22]([NH:27]C(=O)OC(C)(C)C)[CH:23]=[CH:24][C:25]=2[CH3:26])=[O:18])[N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12>S(C)C.ClCCl>[NH2:27][C:22]1[CH:23]=[CH:24][C:25]([CH3:26])=[C:20]([NH:19][C:17]([C:10]2[N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]3=[N:8][CH:9]=2)=[O:18])[CH:21]=1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71280675Tert-butyl 3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenylcarbamate

Produkt 1

HCID 86677450N-(5-amino-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1068Dimethyl SulfideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (50 mL) was added to a stirred suspension of tert-butyl 3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenylcarbamate (66) in Me2S (5 mL) and dichloromethane (10 mL). After 2 hours the solution was evaporated and partitioned with dichloromethane and saturated NaHCO3. The aqueous layer was extracted several times with dichloromethane and the combined organic layers were dried over Na2SO4. N-(5-amino-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (67) was isolated and used without further purification. 1H NMR (400 MHz, CDCl3) δ 9.44 (d, J=6.8 Hz, 1 H), 8.05 (s, 1 H), 7.67 (d, J=8.8 Hz, 1 H), 7.38-7.33 (m, 2 H), 6.98-6.94 (m, 2 H), 2.19 (s, 3 H). MS m/z 267.1 (M+1)+.

Aufarbeitung

  1. customAfter 2 hours the solution was evaporated
  2. custompartitioned with dichloromethane and saturated NaHCO3
  3. extractionThe aqueous layer was extracted several times with dichloromethane
  4. dry with materialthe combined organic layers were dried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-2d0fa3e9ed0f48e5bab20ae08561330d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023839B2

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