Triethylamine → 5-(3,4-Dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (pyridin-2-ylmethyl)-amide

HRID 11886

反応式

HRID 11886 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]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=N1.[Cl:28][C:29]1[CH:30]=[C:31]([C:36]2[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[N:39]3[N:46]=[C:47]([C:49](O)=[O:50])[CH:48]=[C:38]3[N:37]=2)[CH:32]=[CH:33][C:34]=1[Cl:35].N1C=CC=CC=1CN.C(N(CC)CC)C>O1CCCC1.C(OCC)C>[N:10]1[CH:11]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:12][NH:8][C:49]([C:47]1[CH:48]=[C:38]2[N:37]=[C:36]([C:31]3[CH:32]=[CH:33][C:34]([Cl:35])=[C:29]([Cl:28])[CH:30]=3)[CH:41]=[C:40]([C:42]([F:43])([F:44])[F:45])[N:39]2[N:46]=1)=[O:50]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10836755-(3,4-Dichlorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

生成物 1

HCID 121332275-(3,4-Dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (pyridin-2-ylmethyl)-amide収率 59.1%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.141 g, 0.319 mmol) was added to a suspension of 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.100 g, 0.265 mmol) and C-Pyridin-2-yl-methylamine (0.033 mL, 0.319 mmol) in tetrahydrofuran (10 mL) containing triethylamine (0.111 mL, 0.795 mmol). The reaction mixture was stirred overnight at room temperature, diluted with ethyl ether (10 mL) and washed with a saturated aqueous solution of sodium bicarbonate (10 mL). The organic layer was collected, concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel to give 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (pyridin-2-ylmethyl)-amide (0.073 g, 59%)

後処理

  1. washwashed with a saturated aqueous solution of sodium bicarbonate (10 mL)
  2. customThe organic layer was collected
  3. concentrationconcentrated under reduced pressure
  4. customthe crude product was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-90de7fa601fe410ebfb5c3e3361413d4
出典データセット
uspto-grants-2006_08
特許番号
US07098335B2

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