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

HRID 570325ノート

反応式

HRID 570325 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1068Dimethyl Sulfide溶媒HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-2d0fa3e9ed0f48e5bab20ae08561330d
出典データセット
uspto-grants-2015_05
特許番号
US09023839B2

反応ノート

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