1,2-Dimethoxyethane → 3-[8-(4-p-Tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine

HRID 1372928

반응식

HRID 1372928 반응식
Br[C:2]1[N:3]=[C:4]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[N:13]=[CH:12]2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.Cl.[NH2:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:19]1([CH3:22])[CH:20]=[CH:21][C:16]([C:14]2[N:13]=[CH:12][N:11]([C:4]3[C:5]4[N:6]([CH:8]=[CH:9][N:10]=4)[CH:7]=[C:2]([C:29]4[CH:30]=[C:25]([NH2:24])[CH:26]=[CH:27][CH:28]=4)[N:3]=3)[CH:15]=2)=[CH:17][CH:18]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27632413-Aminophenylboronic acid hydrochlorideHCID 210728866-Bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazine

생성물 1

HCID 210728853-[8-(4-p-Tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine수율 66.7%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A mixture of 6-bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazine (4) (870 mg), 3-aminophenylboronic acid hydrochloride (511 mg), tetrakis(triphenylphosphine) palladium (Pd(PPh3)4) (142 mg), 1 M aqueous sodium carbonate (Na2CO3) (7.4ml), and 1,2-dimethoxyethane (DME) (35 ml) is heated at 90 ° C. for 16 hours. The mixture is cooled to rt, treated with water (50 ml) and extracted with ethyl acetate (3×80 ml). The extracts are washed with water (1×50 ml) and brine (1×50 ml), dried over MgSO4, and evaporated in vacuo to give a semi-solid which is triturated with diethyl ether/methanol (10:1) to give 3-[8-(4-p-Tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine (5) (600 mg) as a cream-colored solid.

후처리

  1. temperatureThe mixture is cooled to rt
  2. extractionextracted with ethyl acetate (3×80 ml)
  3. washThe extracts are washed with water (1×50 ml) and brine (1×50 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customto give a semi-solid which
  7. customis triturated with diethyl ether/methanol (10:1)

출처 및 근거

ORD 기록
ord-a606fcd26b07492dac83b0e6fe2e9fae
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160885B2

연결된 노트

불러오는 중…