Trifluoroacetic acid → N-(4-methylthiazol-2-yl)-2-(piperazin-1-yl)acetamide

HRID 416727노트

반응식

HRID 416727 반응식
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8](=[O:23])[CH2:9][N:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[S:5][CH:6]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8](=[O:23])[CH2:9][N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[S:5][CH:6]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 57897251tert-Butyl 4-(2-(4-methylthiazol-2-ylamino)-2-oxoethyl)piperazine-1-carboxylate

생성물 1

HCID 22164330N-(4-methylthiazol-2-yl)-2-(piperazin-1-yl)acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 4-(2-(4-methylthiazol-2-ylamino)-2-oxoethyl)piperazine-1-carboxylate (0.072 g, 0.21 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid (2.5 ml). The reaction mixture was stirred at room temperature for 1.5 h, then the solvents were removed under reduced pressure to afford N-(4-methylthiazol-2-yl)-2-(piperazin-1-yl)acetamide (a semi-solid material) that was dried in vacuo. To a mixture of this material (supposedly 0.20 mmol) and isopropanol (3.5 ml) was added 2-amino-4,5-dichloro-3-nitropyridine (0.031 g, 0.15 mmol) followed by diisopropylethylamine (0.14 ml, 0.80 mmol). The reaction mixture was stirred at 45° C. for 20 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 20% ethyl acetate in dichloromethane. The title compound was obtained as an orange solid (0.044 g, 54%). 1H-NMR (500 MHz, DMSO-d6) 2.26 (s, 3H, CH3), 2.65 (br s, 4H, piperazine N(CH2)2), 3.10 (br s, 4H, piperazine N(CH2)2), 3.33 (s, 2H, NCH2CO), 6.76 (s, 1H, thiazole 5-H), 6.96 (br s, 2H, NH2), 8.07 (s, 1H, 6-H), 11.75 (s, 1H, CONH);

후처리

  1. customthe solvents were removed under reduced pressure

출처 및 근거

ORD 기록
ord-935f55137c294f71b48481932ed19ef5
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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