Triethylamine → HCID 178431605, 화합물

HRID 1714606노트

반응식

HRID 1714606 반응식
FC(F)(F)C(O)=O.[C:8]1([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:17]=[CH:16][C:15]=2[NH:26][C:27]([C:29]2[NH:30][CH:31]=[C:32]([C:34]#[N:35])[N:33]=2)=[O:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1.CCN(CC)CC.[CH3:43][C:44]1([CH3:51])[O:49][CH2:48][C:47](=O)[CH2:46][O:45]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.O>[C:8]1([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:21][CH2:22][N:23]([CH:47]4[CH2:48][O:49][C:44]([CH3:51])([CH3:43])[O:45][CH2:46]4)[CH2:24][CH2:25]3)[CH:17]=[CH:16][C:15]=2[NH:26][C:27]([C:29]2[NH:30][CH:31]=[C:32]([C:34]#[N:35])[N:33]=2)=[O:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 5049666Sodium triacetoxyborohydrideHCID 1785103834-Cyano-1h-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt

생성물 1

HCID 178431605HCID 178431605, 화합물수율 28.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a slurry of 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt (81 mg, 0.16 mmol, as prepared in Example 14, step (b)) in CH2Cl2 (3 mL) was added NEt3 (33 μL, 0.24 mmol). The solution was then treated with 2,2-dimethyl-[1,3]dioxan-5-one (31 mg, 0.24 mmol) and the reaction was allowed to stir for 3 h. At this time NaBH(OAc)3 (51 mg, 0.24 mmol) was added in one portion, and the reaction was allowed to stir for an additional 4 h. The reaction was diluted with H2O (10 mL) and extracted with EtOAc (2×25 mL). The organic extracts were dried (Na2SO4) and concentrated in vacuo. Purification by silica gel preparative thin layer chromatography (10% MeOH—CHCl3) afforded 22 mg (28%) of the title compound as an off-white semi-solid. Mass spectrum (ESI, m/z): Calcd. for C28H35N5O3, 490.2 (M+H), found 490.6.

후처리

  1. stirringto stir for an additional 4 h
  2. extractionextracted with EtOAc (2×25 mL)
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel preparative thin layer chromatography (10% MeOH—CHCl3)

출처 및 근거

ORD 기록
ord-3fb986260e84472b8503c6706b4bb8f4
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795279B2

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