Dicyclohexylcarbodiimide → 2-Methyl-4-(3-methyl-5-(2-oxo-2-(5-(pyrazin-2-yl)pyridin-2-ylamino)ethyl)pyridin-2-yl)pyridine 1-oxide

HRID 592187ノート

反応式

HRID 592187 の反応式
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH3:19])[C:8]([C:11]2[CH:16]=[CH:15][N+:14]([O-:17])=[C:13]([CH3:18])[CH:12]=2)=[N:9][CH:10]=1)([OH:3])=O.[N:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1[C:26]1[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:18][C:13]1[CH:12]=[C:11]([C:8]2[C:7]([CH3:19])=[CH:6][C:5]([CH2:4][C:1](=[O:3])[NH:32][C:29]3[CH:28]=[CH:27][C:26]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][N:20]=4)=[CH:31][N:30]=3)=[CH:10][N:9]=2)[CH:16]=[CH:15][N+:14]=1[O-:17]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 592592255-(Pyrazin-2-yl)pyridin-2-amineHCID 671347314-(5-(Carboxymethyl)-3-methylpyridin-2-yl)-2-methylpyridine 1-oxide

生成物 1

HCID 584479182-Methyl-4-(3-methyl-5-(2-oxo-2-(5-(pyrazin-2-yl)pyridin-2-ylamino)ethyl)pyridin-2-yl)pyridine 1-oxide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-(5-(carboxymethyl)-3-methylpyridin-2-yl)-2-methylpyridine 1-oxide 156-6 from Step 4 (0.41 mmol), 5-(pyrazin-2-yl)pyridin-2-amine 86-3 (141 mg, 0.82 mmol), 1,3-dicyclohexylcarbodiimide (188 mg, 0.90 mmol) and 4-(dimethylamino)pyridine (16 mg, 0.16 mmol) in DMF (2 mL) was stirred at room temperature for 10 hours. The crude product was filtered to remove the insoluble and the filtrate was purified by reverse phase HPLC to give 2-methyl-4-(3-methyl-5-(2-oxo-2-(5-(pyrazin-2-yl)pyridin-2-ylamino)ethyl)pyridin-2-yl)pyridine 1-oxide 156 as white solid. MS m/z 413.2 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 11.12 (s, 1H), 9.31 (d, 1H), 9.11 (d, 1H), 8.72 (m, 1H), 8.62 (d, 1H), 8.52 (dd, 1H), 8.48 (d, 1H), 8.31 (d, 1H), 8.21 (d, 1H), 7.73 (m, 2H), 7.52 (dd, 1H), 3.86 (s, 2H), 2.41 (s, 3H), 2.40 (s, 3H).

後処理

  1. filtrationThe crude product was filtered
  2. customto remove the insoluble and the filtrate
  3. customwas purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-85b2ced6f51e4bd8b0ed8dbe853983f4
出典データセット
uspto-grants-2016_01
特許番号
US09238646B2

反応ノート

読み込み中…