1,2-Dichloroethane → N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

HRID 1750643

반응식

HRID 1750643 반응식
Cl.C[N:3]([C:10]1[CH:15]=[N:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1)[C@H:4]1[CH2:8][CH2:7][CH2:6][C@@H:5]1[NH2:9].[N:20]1[N:21]([C:25]2[C:26]([C:31]([OH:33])=O)=[N:27][CH:28]=[CH:29][CH:30]=2)[N:22]=[CH:23][CH:24]=1.[CH2:34](Cl)CCl.N1C2C(=NC=CC=2)N(O)N=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:34][C:15]1[C:10]([NH:3][C@H:4]2[CH2:8][CH2:7][CH2:6][C@@H:5]2[NH:9][C:31]([C:26]2[C:25]([N:21]3[N:22]=[CH:23][CH:24]=[N:20]3)=[CH:30][CH:29]=[CH:28][N:27]=2)=[O:33])=[N:11][CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[N:14]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 667422883-[1,2,3]Triazol-2-yl-pyridine-2-carboxylic acidHCID 118308127(1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2회

생성물 1

HCID 118308165N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (1S,2S)-1-N-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 23; 60 mg, 0.20 mmol), 3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxylic acid (CAS number 1252907-86-0; 40 mg, 0.21 mmol), EDC (58 mg, 0.30 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (41 mg, 0.30 mmol) and triethylamine (0.085 ml, 0.61 mmol) in DCM (1 ml) was stirred at room temperature over the weekend. The reaction was concentrated in vacuo and was then purified by column chromatography (basic silica, 20 to 100% ethyl acetate/petrol) followed by column chromatography (silica, 0 to 100% ethyl acetate/petrol) to afford the title compound.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. customwas then purified by column chromatography (basic silica, 20 to 100% ethyl acetate/petrol)

출처 및 근거

ORD 기록
ord-96d3eb83dd814945b9279c16465daaa3
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156829B2

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