Dimethylamine → HCID 178484630、化合物

HRID 1433212ノート

反応式

HRID 1433212 の反応式
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:32]=[CH:31][C:15]2[NH:16][C:17]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:18][C:14]=2[CH:13]=1)[C:3]([OH:5])=O.[CH:33]([N:36](C(C)C)[CH2:37]C)(C)C.CNC>CN(C=O)C>[CH3:33][N:36]([CH3:37])[C:3](=[O:5])[CH:2]([OH:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:32]=[CH:31][C:15]2[NH:16][C:17]([CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=3)=[N:18][C:14]=2[CH:13]=1

参加物

5

反応物 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 178525951HCID 178525951、化合物

生成物 1

HCID 178484630HCID 178484630、化合物収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of hydroxy-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-acetic acid (0.030 g, 0.0678 mmol) in DMF (0.5 mL) was added (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) (0.033 g, 0.0745 mmol), diisopropylethylamine (DIPEA) (0.05 mL, 0.272 mmol), and dimethylamine (0.05 mL, 0.102 mmol, 2.0M solution in THF). After stirring for 12 hours, the crude product was purified by chromatography (silica, CH2Cl2: MeOH, 5:1) to afford the title compound as a white solid (0.028 g, 83%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.71-7.67 (m, 2H), 7.63 (d, 2H, J=8.4 Hz), 7.41-7.37 (m, 5H), 7.25 (d, 2H, J=8.8 Hz), 5.46 (s, 2H), 5.24 (s, 1H), 2.85 (s, 3H), 2.36 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C25H23F3N3O3: 470.5 (M+H), Found 470.3.

後処理

  1. customthe crude product was purified by chromatography (silica, CH2Cl2: MeOH, 5:1)

出典と根拠

ORDレコード
ord-d832f1a777d4482cba8c775767e3342d
出典データセット
uspto-grants-2009_11
特許番号
US07612211B2

反応ノート

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