홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

4-Cyanopiperidine → N-({3'-[(4-Cyano-1-piperidinyl)methyl]-6-fluoro-3-biphenylyl}methyl)-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

HRID 564643
노트
인쇄 미리보기

반응식

HRID 564643 반응식
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:48][CH3:49])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:31][CH2:32][C:33]4[CH:34]=[C:35]([C:40]5[CH:45]=[CH:44][CH:43]=[C:42]([CH:46]=O)[CH:41]=5)[C:36]([F:39])=[CH:37][CH:38]=4)=[O:30])[CH:24]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[NH:50]1[CH2:55][CH2:54][CH:53]([C:56]#[N:57])[CH2:52][CH2:51]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:56]([CH:53]1[CH2:54][CH2:55][N:50]([CH2:46][C:42]2[CH:41]=[C:40]([C:35]3[C:36]([F:39])=[CH:37][CH:38]=[C:33]([CH2:32][NH:31][C:29]([C:25]4[CH:26]=[CH:27][CH:28]=[C:23]([C:21]([NH:20][CH2:19][C:10]5[C:11]([NH:12][CH:13]6[CH2:14][CH2:15][O:16][CH2:17][CH2:18]6)=[C:6]6[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]6=[N:8][C:9]=5[CH2:48][CH3:49])=[O:22])[CH:24]=4)=[O:30])[CH:34]=3)[CH:45]=[CH:44][CH:43]=2)[CH2:51][CH2:52]1)#[N:57]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1382234-CyanopiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 57813252N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-[(6-fluoro-3'-formyl-3-biphenylyl)methyl]-1,3-benzenedicarboxamide

생성물 1

HCID 57813480N-({3'-[(4-Cyano-1-piperidinyl)methyl]-6-fluoro-3-biphenylyl}methyl)-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide
수율 28.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-[(6-fluoro-3′-formyl-3-biphenylyl)methyl]-1,3-benzenedicarboxamide (82 mg, 0.129 mmol) in DCM (2.58 mL) was added 4-piperidinecarbonitrile (14.21 mg, 0.129 mmol), NaBH(OAc)3 (41.0 mg, 0.193 mmol). This mixture was stirred at room temperature for 19 h. The reaction mixture was washed with H2O (1 mL), concentrated, purified using a Gilson HPLC (with 0.1% TFA), and basified with an amine cartridge to afford 0.0274 g (28%) of the title compound. LC-MS m/z 757 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.41 (t, J=7.53 Hz, 3 H) 1.49 (t, J=7.15 Hz, 3 H) 1.82-1.93 (m, J=13.05 Hz, 2 H) 1.96-2.38 (m, 6 H) 2.92-3.20 (m, 4 H) 3.22-3.29 (m, 1 H) 3.49-3.73 (m, 4 H) 4.00-4.09 (m, 2 H) 4.31-4.52 (m, 5 H) 4.62 (s, 2 H) 4.72 (s, 2 H) 7.20 (dd, J=10.54, 8.53 Hz, 1 H) 7.39-7.46 (m, 1 H) 7.50-7.65 (m, 4 H) 7.67-7.77 (m, 2 H) 8.05 (d, J=8.03 Hz, 2 H) 8.30 (s, 1 H) 8.39 (t, J=1.51 Hz, 1 H).

후처리

  1. washThe reaction mixture was washed with H2O (1 mL)
  2. concentrationconcentrated
  3. custompurified

출처 및 근거

ORD 기록
ord-c98bb4a472a04f89bde161cb350badd5
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067408B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트