Aniline → HCID 57742714, 화합물

HRID 911878노트

반응식

HRID 911878 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:14][C:15]1[CH:16]=[C:17]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH2:27]Cl)[N:26]=2)=[N:19][CH:20]=1>CN1C(=O)CCC1>[Br:14][C:15]1[CH:16]=[C:17]([O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:18]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH2:27][NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:26]=2)=[N:19][CH:20]=1

참가 물질

5

반응물 3

HCID 6115AnilineHCID 10796Cesium carbonateHCID 57742594HCID 57742594, 화합물

생성물 1

HCID 57742714HCID 57742714, 화합물수율 29.2%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Aniline (0.0352 g, 0.378 mmol) was dissolved in 2 mL NMP at ambient temperature. Cs2CO3 (0.0246 g, 0.0756 mmol) and solid 5-bromo-N-(4-(chloromethyl)thiazol-2-yl)-3-phenoxypyridin-2-amine (0.030 g, 0.0756 mmol) were added to the reaction and the mixture was stirred at ambient temperature overnight. The reaction was concentrated to dryness, dissolved in CH2Cl2, washed with water, dried over Na2SO4, and concentrated to dryness. The residue was purified by preparative HPLC to give the title compound (0.010 g, 29.2% yield) as tan solids. 1H NMR (CDCl3) δ 4.34 (br s, 3H), 6.67-6.74 (m, 4H), 7.07 (d, J=8.0 Hz, 2H), 7.13 (d, J=1.8 Hz, 1H), 7.18 (t, J=7.7 Hz, 2H), 7.24-7.27 (m, 1H), 7.43 (t, J=7.9 Hz, 2H), 8.13 (d, J=1.6 Hz, 1H), 8.74 (br s, 1H).

후처리

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-d0ae3af195f14bae924e856133acf28a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022223B2

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