1-(Methylamino)adamantane → 5-Benzyl-1,3-dimethyl-1h-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide

HRID 2279643노트

반응식

HRID 2279643 반응식
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2C=CC=CC=2N=N1.[CH2:28]([C:35]1[N:39]([CH3:40])[N:38]=[C:37]([CH3:41])[C:36]=1[C:42]([OH:44])=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:45]12(NC)[CH2:54][CH:49]3[CH2:50][CH:51]([CH2:53][CH:47]([CH2:48]3)[CH2:46]1)[CH2:52]2.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:45]12([CH2:12][NH:8][C:42]([C:36]3[C:37]([CH3:41])=[N:38][N:39]([CH3:40])[C:35]=3[CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:44])[CH2:46][CH:47]3[CH2:48][CH:49]([CH2:50][CH:51]([CH2:53]3)[CH2:52]1)[CH2:54]2

참가 물질

8

반응물 5

HCID 194761-(Methylamino)adamantaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 595799845-Benzyl-1,3-dimethyl-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 595798435-Benzyl-1,3-dimethyl-1h-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

BOP (44 mg, 0.1 mmol) is added to a solution of 5-benzyl-1,3-dimethyl-1H pyrazole-4-carboxylic acid (20 mg, 0.087 mmol), admantan-1-yl-methylamine (15 mg, 0.09 mmol), HOBt (5 mg) and DIEA (17 μL, 0.1 mmol) in DMF (0.5 mL) at it. The mixture is stirred for 14 h. H2O is added, and the mixture is extracted with EtOAc (3×10 mL). The organic phase is dried. The title compound is obtained by PTLC using 20% EtOAc in hexane. 1H NMR (CDCl3): 7.29-7.21 (m, 3H), 7.12-7.11 (in, 2H), 5.39 (m, 1H), 4.33 (s, 2H), 3.65 (s, 3H), 3.07 (m, 2H), 2.46 (s, 3H), 1.94 (m, 3H), 1.70-1.56 (m, 12H). MS (M+1)=378.22; RT=1.67 min. *IC50.

후처리

  1. extractionthe mixture is extracted with EtOAc (3×10 mL)
  2. customThe organic phase is dried

출처 및 근거

ORD 기록
ord-5454bb327f74433781030c2e83611519
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133204B2

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