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

HRID 1497875노트

반응식

HRID 1497875 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1068Dimethyl Sulfide용매HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c4a77375fc2b4695a13e8268fdea9b7c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199981B2

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