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 2174958ノート

反応式

HRID 2174958 の反応式
[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

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 56947515Panulisib

生成物 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-5955bed43a3c459d88b327b5181271f4
出典データセット
uspto-grants-2015_06
特許番号
US09062046B2

反応ノート

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