Triethylamine → HCID 86674652, 화합물

HRID 62458

반응식

HRID 62458 반응식
[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

참가 물질

8

반응물 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

생성물 1

HCID 86674652HCID 86674652, 화합물수율 99%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c34b64f6ed44ffa95a8318344aab70b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446130B2

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