Sodium hydride → N-(8-(6-(benzylamino)-5-(trifluoromethyl)pyridin-3-yl)-1-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide

HRID 2174958노트

반응식

HRID 2174958 반응식
[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:19]=[CH:18][C:17]3[N:16]=[CH:15][C:14]4[N:20]([CH3:37])[C:21](=[N:34][C:35]#[N:36])[N:22]([C:23]5[CH:24]=[N:25][C:26]([C:29]([C:32]#[N:33])([CH3:31])[CH3:30])=[CH:27][CH:28]=5)[C:13]=4[C:12]=3[CH:11]=2)=[CH:6][C:5]=1[C:38]([F:41])([F:40])[F:39]>C1COCC1>[CH2:7]([NH:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:19]=[CH:18][C:17]3[N:16]=[CH:15][C:14]4[N:20]([CH3:37])[C:21](=[N:34][C:35]#[N:36])[N:22]([C:23]5[CH:24]=[N:25][C:26]([C:29]([C:32]#[N:33])([CH3:30])[CH3:31])=[CH:27][CH:28]=5)[C:13]=4[C:12]=3[CH:11]=2)=[CH:6][C:5]=1[C:38]([F:40])([F:39])[F:41])[C:10]1[CH:19]=[CH:18][CH:17]=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 56947515Panulisib

생성물 1

HCID 56599111N-(8-(6-(benzylamino)-5-(trifluoromethyl)pyridin-3-yl)-1-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (0.521 mmol) was added to a solution of N-(8-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-1-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide (Example 5, 0.474 mmol) in dry THF. The reaction mixture was stirred for 20 minutes, followed by the addition of dibenzylchloro phosphate (0.474 mmol). The reaction mixture was further stirred at RT for 24 h. The crude product was filtered and purified (silica gel column, MeOH/CHCl3 as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 9.22 (s, 1H), 9.06 (d, J=2.4 Hz, 1H), 8.41 (dd, J=8.4, 2.4 Hz, 1H), 8.16 (d, J=9.0 Hz, 1H), 8.08 (bs, 1H), 8.01-7.97 (m, 2H), 7.81 (bs, 1H), 7.46 (m, 1H), 7.34-7.21 (m, 5H), 6.86 (d, J=1.8 Hz, 1H), 4.67 (d, 2H), 3.91 (s, 3H), 1.74 (s, 3H), 1.73 (s, 3H); MS (m/z): 618.3 (M+1)+.

후처리

  1. stirringThe reaction mixture was further stirred at RT for 24 h
  2. filtrationThe crude product was filtered
  3. custompurified (silica gel column, MeOH/CHCl3 as eluent)

출처 및 근거

ORD 기록
ord-5955bed43a3c459d88b327b5181271f4
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062046B2

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