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Diisopropylethylamine → N-[3-(4-Cyclohexylcarbamoyl-4-fluoro-piperidin-1-ylmethyl)-phenyl]-5-methyl-nicotinamide

HRID 1486747
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HRID 1486747 반응식
[CH:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1)=O.Cl.[CH:20]1([NH:26][C:27]([C:29]2([F:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:20]1([NH:26][C:27]([C:29]2([F:35])[CH2:34][CH2:33][N:32]([CH2:1][C:3]3[CH:4]=[C:5]([NH:9][C:10](=[O:18])[C:11]4[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][CH:12]=4)[CH:6]=[CH:7][CH:8]=3)[CH2:31][CH2:30]2)=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86706560N-(3-Formyl-phenyl)-5-methyl-nicotinamideHCID 867065644-Fluoro-piperidine-4-carboxylic acid cyclohexylamide hydrochloride

생성물 1

HCID 86706563N-[3-(4-Cyclohexylcarbamoyl-4-fluoro-piperidin-1-ylmethyl)-phenyl]-5-methyl-nicotinamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of N-(3-formyl-phenyl)-5-methyl-nicotinamide L-1 (60 mg, 0.25 mmol) and 4-fluoro-piperidine-4-carboxylic acid cyclohexylamide hydrochloride (66 mg, 0.25 mmol) in DCM (3 mL) is treated with DIPEA (0.128 mL, 0.75 mmol). Sodium triacetoxyborohydride (132 mg, 0.62 mmol) is added at once and the mixture is stirred at RT for 18 h. The mixture is diluted with DCM (5 mL) and washed twice with aq. sat. NaHCO3 (5 mL). The organic phase is dried over MgSO4 and evaporated. The residue is dissolved in acetonitrile and purified by prep HPLC E, delivering the title compound as a colorless powder, LC-MS A: tR=0.62 min; [M+H]+=453.4. 1H-NMR (CDCl3): δ 1-1.4 (m, 5H), 1.6-1.8 (m, 6H), 1.9-2.1 (m, 2H), 2.2-2.4 (m, 4H), 3.45 (s, 3H), 2.7-2.8 (m, 2H), 3.7-3.8 (m, 1H), 6.28 (t, J=6.5, 1H), 7.15 (d, J=8, 1H), 7.35 (t, J=8, 1H), 7.55 (s, 1H), 7.73 (d, J=8, 1H), 8.05 (s, 1H), 8.12 (s, 1H), 8.61 (s, 1H), 8.93 (s, 1H).

후처리

  1. washwashed twice with aq. sat. NaHCO3 (5 mL)
  2. dry with materialThe organic phase is dried over MgSO4
  3. customevaporated
  4. dissolutionThe residue is dissolved in acetonitrile
  5. custompurified by prep HPLC E

출처 및 근거

ORD 기록
ord-0aa82bfad9424cf39de4c1fcc6bfd2fe
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09428456B2

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