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

HRID 1045432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1045432
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, 1H), 8.05 (s, 1H), 7.67 (d, J=8.8 Hz, 1H), 7.38-7.33 (m, 2H), 6.98-6.94 (m, 2H), 2.19 (s, 3H). 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-c28c10fa021e45f79df5e04ecf5771db
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569283B2

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