Triethylamine → N-[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]-1H-imidazole-1-carboxamide

HRID 1715275노트

반응식

HRID 1715275 반응식
FC(F)(F)C([O-])=O.[CH3:8][C:9]1[N:10]=[C:11]([NH2:27])[S:12][C:13]=1[C:14]1[N:15]=[C:16]([C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[S:17][CH:18]=1.[CH:28]1[N:32]=[CH:31][N:30]([C:33](N2C=NC=C2)=[O:34])[CH:29]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH3:8][C:9]1[N:10]=[C:11]([NH:27][C:33]([N:30]2[CH:29]=[CH:28][N:32]=[CH:31]2)=[O:34])[S:12][C:13]=1[C:14]1[N:15]=[C:16]([C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[S:17][CH:18]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 84468TrifluoroacetateHCID 866219884'-Methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-amine

생성물 1

HCID 59465567N-[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]-1H-imidazole-1-carboxamide수율 79%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

Trifluoroacetate salt of 4′-methyl-2-(morpholin-4-ylcarbonyl)-4,5′-bi-1,3-thiazol-2′-amine, prepared in Step II, described above (142.4 mg; 0.34 mmol; 1 eq.) is suspended in dry DCM (5 ml). CDI (108.8 mg; 0.68 mmol; 2 eq.) and triethylamine (511; 0.37 mmol; 1.10 eq.) are added. Some DMF (0.30 ml) is added to improve the solubility of the starting material. The mixture is stirred overnight at 40° C. A precipitate is formed. It is filtrated, washed with diethyl ether, affording N-[4′-methyl-2-(morpholin-4-ylcarbonyl)-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide (107.1 mg; 79%) which is used as such in the next step without further purification.

후처리

  1. customA precipitate is formed
  2. filtrationIt is filtrated
  3. washwashed with diethyl ether

출처 및 근거

ORD 기록
ord-0cd05f2915bb4647b765a9619b9e6bf6
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799814B2

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