Dicyclohexylcarbodiimide → 2,3-Dimethylimidazo[1,2-a]pyrid-7-ylamine

HRID 1944003ノート

反応式

HRID 1944003 の反応式
FC(F)(F)C1C=C2C(=CC=1)[N:8](CC1C=CC=C(F)C=1)C(C(O)=O)=C2.[CH:25]1([N:31]=[C:32]=[N:33][CH:34]2[CH2:39][CH2:38]CC[CH2:35]2)[CH2:30][CH2:29][CH2:28]CC1.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[CH3:35][C:34]1[N:33]=[C:32]2[CH:28]=[C:29]([NH2:8])[CH:30]=[CH:25][N:31]2[C:39]=1[CH3:38]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 574315325-trifluoromethyl-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid

生成物 1

HCID 668633632,3-Dimethylimidazo[1,2-a]pyrid-7-ylamine収率 150.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution, stirred at 20° C. under an inert atmosphere, of 1 g (2.96 mmol) of 5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylic acid (WO 2006/072736) in 70 mL of DMF are added 0.74 g (3.56 mmol) of dicyclohexylcarbodiimide (DCC) and 0.48 g (3.56 mmol) of 1-hydroxybenzotriazole hydrate (HOBT). The reaction mixture is stirred at room temperature for 30 minutes. 0.7 g (4.45 mmol) of 2,3-dimethylimidazo[1,2-a]pyrid-7-ylamine, obtained according to the protocol described in step 14.4, and 100 mg of dimethylaminopyridine (DMAP) are then added to the reaction mixture. After stirring for 12 hours at 50° C., the reaction mixture is concentrated to dryness. The residue obtained is taken up in a mixture of 50 mL of water and 50 mL of ethyl acetate. The phases are separated by settling and the aqueous phase is extracted with 200 mL of ethyl acetate. The combined organic phases are dried over sodium sulfate and then concentrated under reduced pressure. The product is isolated after successive purifications by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol. 50 mg of the expected product are thus obtained.

出典と根拠

ORDレコード
ord-213f7397eaa34f02a432c4529fd7e36f
出典データセット
uspto-grants-2013_03
特許番号
US08394820B2

反応ノート

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