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Triethylamine → N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxamide

HRID 1678450
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HRID 1678450 반응식
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)[N:3]=1.CCN=C=N[CH2:24][CH2:25][CH2:26][N:27](C)C.C1[CH:31]=[CH:32][C:33]2N(O)N=[N:36][C:34]=2C=1.[CH2:40](N(CC)CC)C.BrC1C=CC(CN)=C(O[C:57]([F:60])([F:59])[F:58])C=1>ClCCl>[C:26]([C:25]1[CH:24]=[CH:40][C:33]([CH2:34][NH:36][C:16]([CH:13]2[CH2:12][CH2:11][N:10]([C:4]3[N:3]=[C:2]([CH3:1])[N:7]=[C:6]([NH:8][CH3:9])[N:5]=3)[CH2:15][CH2:14]2)=[O:18])=[C:32]([C:57]([F:60])([F:59])[F:58])[CH:31]=1)#[N:27]
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참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 594477131-[4-Methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acidHCID 59447718(4-Bromo-2-(trifluoromethoxy)phenyl)methanamine

생성물 1

HCID 25261292
N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxamide
수율 5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid (100 mg, 0.4 mmol) was dissolved in 3 mL of dichloromethane and treated with EDCI (115 mg, 0.6 mmol), HOBt (65 mg, 0.48 mmol), triethylamine (0.44 mL, 3.2 mmol), and 1-{4-bromo-2-[(trifluoromethyl)oxy]phenyl}methanamine (152 mg, 0.4 mmol) at 8° C. for 4 days. The reaction mixture was concentrated and purified by preparative HPLC to provide N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxamide (3.5 mg, 0.02 mmol, 2%) as a white solid. MS (ES+): m/e 503, 505 [M+H]+. 1H NMR (400 MHz, methanol-D4) 7.4 (m, 2H), 7.2 (d, 1H), 4.8 (2H under MeOH peak), 4.3 (s, 2H), 3.1 (m, 2H), 2.9 (s, 3H), 2.5 (m, 1H), 2.3 (s, 3H), 1.8 (m, 2H), 1.6 (m, 2H)

후처리

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-2f9191f159c344dfa7129a1fdd07100c
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08008483B2

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