Pyridine → 3,3-dimethyl-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2,3-dihydrobenzofuran-6-carboxamide

HRID 1256407ノート

反応式

HRID 1256407 の反応式
[CH3:1][C:2]1([CH3:14])[C:6]2[CH:7]=[CH:8][C:9]([C:11](Cl)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3]1.N1C=CC=CC=1.[CH3:21][C:22]1[CH:37]=[C:25]2[N:26]=[C:27]([NH2:36])[CH:28]=[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:24]2[N:23]=1>C(#N)C.O>[CH3:1][C:2]1([CH3:14])[C:6]2[CH:7]=[CH:8][C:9]([C:11]([NH:36][C:27]3[CH:28]=[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:24]4[N:23]=[C:22]([CH3:21])[CH:37]=[C:25]4[N:26]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3]1

参加物

6

反応物 3

HCID 1049PyridineHCID 582071812-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amineHCID 866522793,3-Dimethyl-2,3-dihydrobenzofuran-6-carbonyl chloride

生成物 1

HCID 670643233,3-dimethyl-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2,3-dihydrobenzofuran-6-carboxamide収率 11%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

In a 25 ml pear flask containing crude 3,3-dimethyl-2,3-dihydrobenzofuran-6-carbonyl chloride (25 mg, 0.12 mmol) was added pyridine (1 mL), immediately followed by 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 26.9 mg, 0.120 mmol). The mixture was stirred at room temperature for ˜16 h. The reaction mixture was partitioned between saturated NaHCO3 and ethyl acetate, and the aqueous layer was extracted one more time with ethyl acetate. Combined organic layers were washed once more with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by SiO2 (20% EtOAc, second spot from the top) to give an off-white solid. To facilitate transfer of the small amount of product, the solid was dissolved in 0.5 mL of acetonitrile, and then suspended in 15 mL of water. Lyophilization of the mixture gave the titled product (5.1 mg, 11% yield). 1H NMR (CHLOROFORM-d) δ: 8.58 (s, 1H), 8.08-8.15 (m, 3H), 7.53-7.59 (m, 3H), 7.46 (dd, J=7.7, 1.6 Hz, 1H), 7.34 (d, J=1.3 Hz, 1H), 7.22 (d, J=7.8 Hz, 1H), 6.28 (s, 1H), 4.31-4.34 (m, 2H), 2.50 (s, 3H), 1.36-1.42 (m, 6H); ESI-MS: m/z 399.4 (M+H)+.

後処理

  1. customThe reaction mixture was partitioned between saturated NaHCO3 and ethyl acetate
  2. extractionthe aqueous layer was extracted one more time with ethyl acetate
  3. washCombined organic layers were washed once more with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by SiO2 (20% EtOAc, second spot from the top)
  8. customto give an off-white solid

出典と根拠

ORDレコード
ord-d939e4d7b4384ae888d12c3da7d74e95
出典データセット
uspto-grants-2013_06
特許番号
US08461163B2

反応ノート

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