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

HRID 1715293
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인쇄 미리보기

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HRID 1715293 반응식
C(N(CC)CC)C.[NH2:8][C:9]1[S:10][C:11]([C:15]2[N:16]=[C:17]([CH2:20][C:21]#[N:22])[S:18][CH:19]=2)=[C:12]([CH3:14])[N:13]=1.[CH:23]1[N:27]=[CH:26][N:25]([C:28](N2C=NC=C2)=[O:29])[CH:24]=1.CN(C=O)C>C(Cl)Cl>[C:21]([CH2:20][C:17]1[S:18][CH:19]=[C:15]([C:11]2[S:10][C:9]([NH:8][C:28]([N:25]3[CH:24]=[CH:23][N:27]=[CH:26]3)=[O:29])=[N:13][C:12]=2[CH3:14])[N:16]=1)#[N:22]
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 59465553(2'-Amino-4'-methyl-4,5'-bi-1,3-thiazol-2-yl)acetonitrile

생성물 1

HCID 59465544N-[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]-1H-imidazole-1-carboxamide

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

반응 조건

온도
45 °C

실험 절차

Triethylamine (0.65 ml; 4.69 mmol; 1.49 eq.) is added to a suspension of (2′-amino-4′-methyl-4,5′-bi-1,3-thiazol-2-yl)acetonitrile (1 000 mg; 3.15 mmol; 1 eq.) and CDI (1 372.3 mg; 8.46 mmol; 2.68 eq.) in dry DCM (65 ml). DMF (4 ml) is added and the mixture is heated at 45° C. for one night. The reaction is cooled down to rt. The resulting precipitate is filtered and washed with Et2O, affording N-[2-(cyanomethyl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide, which is used in the next step without further purification (822.8 mg; 79%).

후처리

  1. temperatureThe reaction is cooled down to rt
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with Et2O

출처 및 근거

ORD 기록
ord-6836d492f8d64d95968ef396ef1dd37d
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07799814B2

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