2-Chlorobenzyl chloroformate → HCID 11584392, 화합물

HRID 1432428노트

반응식

HRID 1432428 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:3].[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]3[N:26]=[C:25]([CH:27]4[CH2:32][CH2:31][N:30](S(CC5C=CC=CC=5)(=O)=O)[CH2:29][CH2:28]4)[NH:24][C:23]=3[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=3)=[CH:21][C:16]=2[O:15][CH2:14]1>C1COCC1.C(=O)(O)[O-].[Na+]>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][O:4][C:2]([N:30]1[CH2:29][CH2:28][CH:27]([C:25]2[NH:24][C:23]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=3)=[C:22]([C:20]3[CH:19]=[CH:18][C:17]4[O:13][CH2:14][O:15][C:16]=4[CH:21]=3)[N:26]=2)[CH2:32][CH2:31]1)=[O:3]

참가 물질

5

반응물 2

HCID 40723422-Chlorobenzyl chloroformateHCID 10345947HCID 10345947, 화합물

생성물 1

HCID 11584392HCID 11584392, 화합물수율 85.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

2-Chlorobenzyl chloroformate (0.011 mL, 0.070 mmol) was added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-pyridine (0.021 g, 0.059 mmol; prepared as described in Example 11) in a mixture of THF (3 mL) and 2 M sodium bicarbonate aqueous solution (0.3 mL). The mixture was stirred at room temperature for 2 hours. Mixture was partitioned between ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated. HPLC purification eluting with acetonitrile:water gave 0.026 g (70%) of the title compound as a yellow solid. MS (ESP+) m/z 517.03 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.60 (m, 1H), 7.81 (m, 1H), 7.60 (d, 1H, J=8.2 Hz), 7.39 (m, 3H), 7.27 (m, 2H), 7.07 (dd, 1H, J=8.1, 1.8 Hz), 6.99 (d, 1H, J=1.8 Hz), 6.90 (d, 1H, J=8.1 Hz), 6.05 (s, 2H), 5.24 (s, 2H), 4.36 (m, 2H), 3.48 (m, 1H), 2.98 (m, 2H), 2.17 (m, 2H), 1.86 (m, 2H).

후처리

  1. customMixture was partitioned between ethyl acetate and water
  2. washThe organic solution was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customHPLC purification
  7. washeluting with acetonitrile

출처 및 근거

ORD 기록
ord-c4025974f2e744aaa92e95372d3a30cf
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612094B2

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