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

HRID 2279643ノート

反応式

HRID 2279643 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5454bb327f74433781030c2e83611519
出典データセット
uspto-grants-2015_09
特許番号
US09133204B2

反応ノート

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