Imidazole → 2-Imidazol-1-yl-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile

HRID 1868300노트

반응식

HRID 1868300 반응식
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([O-])([O-])=O.[Cs+].[Cs+].I[C:13]1[S:21][C:20]2[C:19]([C:22]#[N:23])=[CH:18][N:17]=[C:16]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:15]=2[CH:14]=1>[Cu]I.O1CCOCC1>[N:1]1([C:13]2[S:21][C:20]3[C:19]([C:22]#[N:23])=[CH:18][N:17]=[C:16]([NH:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[C:15]=3[CH:14]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 18446524HCID 18446524, 화합물

생성물 1

HCID 184465232-Imidazol-1-yl-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile수율 56.3%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

실험 절차

To an oven dried Schlenk tube was added CuI (0.0057 g, 0.030 mmol), imidazole (0.097 g, 1.42 mmol), Cs2CO3 (0.405 g, 1.25 mmol). The tube was evacuated and purged to argon 5 times. Under argon, the tube was supplied with 2-iodo-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile 27 (0.25 g, 0.59 mmol) trans-1,2-cyclohexanediamine (0.014 mL, 0.12 mmol), and dioxane (1 mL). The reaction contents were briefly evacuated and the vessel purged to argon 3 times, then sealed and brought to 110° C. with stirring. After 24 h, 20 mL of CH2Cl2 were added to the cooled reaction. The mixture was filtered and solvents removed in vacuo. Silica gel column chromatography (eluent: 3% MeOH in CH2Cl2) provided 0.12 g of 37. 1H NMR (400 MHz, d6-DMSO) δ 8.57 (t, J=6 Hz, 1H), 8.47 (s, 1H), 8.23 (bs, 1H), 8.00 (s, 1H), 7.71 (bs, 1H), 7.31 (d, J=8 Hz, 2H), 7.21 (bs, 1H), 6.91 (d, J=8 Hz, 2H), 3.74 (s, 3H).

후처리

  1. customTo an oven dried Schlenk tube
  2. customThe tube was evacuated
  3. custompurged to argon 5 times
  4. customThe reaction contents
  5. customwere briefly evacuated
  6. customthe vessel purged to argon 3 times
  7. customsealed
  8. custombrought to 110° C.
  9. addition20 mL of CH2Cl2 were added to the cooled reaction
  10. filtrationThe mixture was filtered
  11. customsolvents removed in vacuo

출처 및 근거

ORD 기록
ord-7a801c634ab4402b89de481fd0ef58fe
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635695B2

반응 노트

불러오는 중…