Triethylamine → HCID 86674652、化合物

HRID 62458

反応式

HRID 62458 の反応式
[C:1](Cl)(=O)[O:2]C(Cl)(Cl)Cl.Cl.[F:10][C:11]([F:22])([F:21])[C:12]1[N:16]2[CH2:17][CH2:18][NH:19][CH2:20][C:15]2=[N:14][N:13]=1.C(N(C(C)C)C(C)C)C.Cl.[Cl:33][C:34]1[C:35]([CH2:40][NH2:41])=[N:36][CH:37]=[CH:38][N:39]=1.C(N(CC)CC)C>O1CCCC1.ClCCl>[Cl:33][C:34]1[C:35]([CH2:40][NH:41][C:1]([N:19]2[CH2:18][CH2:17][N:16]3[C:12]([C:11]([F:21])([F:10])[F:22])=[N:13][N:14]=[C:15]3[CH2:20]2)=[O:2])=[N:36][CH:37]=[CH:38][N:39]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 81531DiisopropylethylamineHCID 119613713-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochlorideHCID 42614233(3-Chloropyrazin-2-yl)methanamine hydrochloride

生成物 1

HCID 86674652HCID 86674652、化合物収率 99%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A stirred solution of trichloromethyl carbonochloridate (1.038 g, 5.25 mmol) in tetrahydrofuran (10 mL) was cooled to 0° C. and a solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride (1 g, 4.37 mmol, J. Med. Chem., 2005, 141) and N-ethyl-N-isopropylpropan-2-amine (1.131 g, 8.75 mmol) in tetrahydrofuran (10 mL) was added slowly in 25 minutes. After stirring at 0° C. for one hour the solids were removed by filtration and the filtrate was concentrated in vaccuo (50° C. bath temperature). The residue was added to a solution of (3-chloropyrazin-2-yl)methanamine hydrochloride (0.788 g, 4.37 mmol) and triethylamine (1.018 g, 10.06 mmol) in dichloromethane (20 mL) and the reaction mixture was stirred for three hours. The solids were removed by filtration and the filtrate was concentrated in vacuo. Purification using column chromatography (silica gel; gradient dichloromethane/methanol 100:0 to 95:5) to afford N-((3-chloropyrazin-2-yl)methyl)-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxamide (1.56 g, 4.31 mmol, 99% yield). LC-MS: C12H11ClF3N7O: 361. found 362.04[M+H]+, RT=0.42 min.

後処理

  1. customwere removed by filtration
  2. concentrationthe filtrate was concentrated in vaccuo (50° C. bath temperature)
  3. stirringthe reaction mixture was stirred for three hours
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification

出典と根拠

ORDレコード
ord-3c34b64f6ed44ffa95a8318344aab70b
出典データセット
uspto-grants-2016_09
特許番号
US09446130B2

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