Acetyl chloride → 7-(4-chlorobenzyl)-1-(2-hydroxyethyl)-3-methyl-8-(3-(3-(trifluoromethoxy)phenoxy)propoxy)1H-purine-2,6(3H,7H)-dione

HRID 2200668노트

반응식

HRID 2200668 반응식
[Cl:1][C:2]1[CH:45]=[CH:44][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][O:19]C4CCCCO4)[C:12](=[O:26])[N:11]([CH3:27])[C:10]=3[N:9]=[C:8]2[O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([O:39][C:40]([F:43])([F:42])[F:41])[CH:34]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][OH:19])[C:12](=[O:26])[N:11]([CH3:27])[C:10]=3[N:9]=[C:8]2[O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([O:39][C:40]([F:43])([F:41])[F:42])[CH:34]=2)=[CH:44][CH:45]=1

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 904033007-(4-chlorobenzyl)-3-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-8-(3-(3-(trifluoromethoxy)phenoxy)propoxy)-1H-purine-2,6(3H,7H)-dione

생성물 1

HCID 904028047-(4-chlorobenzyl)-1-(2-hydroxyethyl)-3-methyl-8-(3-(3-(trifluoromethoxy)phenoxy)propoxy)1H-purine-2,6(3H,7H)-dione수율 39.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 7-(4-chlorobenzyl)-3-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-8-(3-(3-(trifluoromethoxy)phenoxy)propoxy)-1H-purine-2,6(3H,7H)-dione (50 mg, 0.09 mmol,) in ethanol (5 mL) was added acetyl chloride (0.2 mL) at 0° C. The mixture was stirred at room temperature for 1 h; then it was partitioned between ethyl acetate and water. The organic phase was separated and dried over sodium sulfate. This organic layer was then filtered and concentrated to give a crude product which was purified by preparative HPLC to give 7-(4-chlorobenzyl)-1-(2-hydroxyethyl)-3-methyl-8-(3-(3-(trifluoromethoxy)phenoxy)propoxy)1H-purine-2,6(3H,7H)-dione (20 mg, 39.2% yield) as a white solid. 1H-NMR (DMSO-d6) δ 7.40(t, 1H), 7.28-7.33(m, 4H), 6.92(dd, 2H), 6.85(s, 1H), 5.23(s, 2H), 4.76(t, 1H), 4.62(t, 2H), 4.08(t, 2H), 3.93(t, 2H), 3.49(q, 2H), 3.33(s, 3H), 2.18-2.24(m, 2H). LCMS retention time 3.058 min; LCMS MH+ 569.

후처리

  1. customthen it was partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationThis organic layer was then filtered
  5. concentrationconcentrated
  6. customto give a crude product which
  7. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-6687814ef5da4afa8ac98ae5dfa5b6dd
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359359B2

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