Acetic Anhydride → 3-(1-acetylpiperidin-4-yl)-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1852982ノート

反応式

HRID 1852982 の反応式
Cl.[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([CH:19]([CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH2:20][C:21]#[N:22])[CH:18]=3)[N:11]3[CH:29]=[CH:30][N:31]=[C:10]3[CH:9]=2)[CH:5]=[N:4]1.C1C[O:35][CH2:34][CH2:33]1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>C(=O)(O)[O-].[Na+].CCOC(C)=O>[C:34]([N:26]1[CH2:27][CH2:28][CH:23]([CH:19]([N:17]2[CH:18]=[C:14]([C:12]3[N:11]4[CH:29]=[CH:30][N:31]=[C:10]4[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][N:3]([CH3:2])[CH:7]=4)[N:13]=3)[CH:15]=[N:16]2)[CH2:20][C:21]#[N:22])[CH2:24][CH2:25]1)(=[O:35])[CH3:33]

参加物

7

反応物 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 866853073-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-(piperidin-4-yl)propanenitrile hydrochloride

生成物 1

HCID 682307493-(1-acetylpiperidin-4-yl)-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile収率 77.3%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-(piperidin-4-yl)propanenitrile hydrochloride (10.0 mg, 0.021 mmol) was suspended in THF (211 μL, 0.0211 mmol). To this was added triethylamine (8.81 DIPHOS, 0.0632 mmol) to free-base. Acetic anhydride (2.38 μL, 0.0253 mmol) was added and the reaction mixture stirred at ambient temperature for 30 minutes. The reaction mixture was then diluted in saturated sodium bicarbonate and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried with MgSO4, filtered and concentrated in vacuo. Purification of the resulting crude material by reverse phase HPLC using 0-100% acetonitrile/water gradient afforded the title compound (7.2 mg, 77% yield). MS (apci) m/z=444.3 (M+H).

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the resulting crude material by reverse phase

出典と根拠

ORDレコード
ord-a0dcd2ed781343f2a08236443c88c884
出典データセット
uspto-grants-2015_02
特許番号
US08962596B2

反応ノート

読み込み中…