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Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → N-(2-(2-tert-butylphenoxy)pyridin-3-yl)-1H-benzo[d]imidazole-2-carboxamide

HRID 1160235
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HRID 1160235 반응식
[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([N:14]=[C:15]=[O:16])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1C(O)=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:15]([C:22]2[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:21]=2)=[O:16])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

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HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2332402-Benzimidazolecarboxylic acidHCID 574233152-(2-tert-Butylphenoxy)-3-isocyanatopyridine

생성물 1

HCID 67026836N-(2-(2-tert-butylphenoxy)pyridin-3-yl)-1H-benzo[d]imidazole-2-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-(2-tert-butylphenoxy)pyridin-3-amine (1a) (80 mg, 0.33 mmol), 1H-benzo[d]imidazole-2-carboxylic acid (54 mg, 0.33 mmol) and BOP (172 mg, 0.39 mmol) in DMF was stirred at rt for 3 days. LC-MS showed only a small amount of the desired product. The reaction was diluted with EtOAc (15 mL), washed with 1 N HCl solution, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and evaporated to give the crude product. Purification of the crude product by reverse phase preparative HPLC provided Example 71 (12 mg) as a yellow solid. LC-MS m/z 387.2 [M+H]+.

출처 및 근거

ORD 기록
ord-1a096fd2004941f7bf6cacb2fac0e086
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07816382B2

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