Triethylamine → 2-Methoxymethyl-4-[4-(pyrrolidine-1-sulfonyl)-piperazin-1-yl]-pyrimidine

HRID 586176

反応式

HRID 586176 の反応式
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][N:5]=1.C(N(CC)CC)C.[N:23]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:28]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)(=[O:30])=[O:29])[CH2:12][CH2:11]2)[CH:7]=[CH:6][N:5]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 64839021-Pyrrolidinesulfonyl chlorideHCID 109547722-Methoxymethyl-4-piperazin-1-yl-pyrimidine

生成物 1

HCID 223287382-Methoxymethyl-4-[4-(pyrrolidine-1-sulfonyl)-piperazin-1-yl]-pyrimidine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-methoxymethyl-4-piperazin-1-yl-pyrimidine (prepared according to the method of Preparation One, 2.08 g, 10 mmol) and triethylamine (1.01 g, 10 mmol) in tetrahydrofuran (20 mL) was added N-pyrrolidinesulfonyl chloride (1.69 g, 10 mmol) at 0° C. and stirred for 3 h at ambient temperature. The mixture was diluted with ethyl acetate and washed twice with water. The organic layer was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated to an oil which was purified by flash chromatography (95:5 dichloromethane:methanol) to give the title compound of Example 121, Step A as a clear oil, 3.24 g (93%). 1H NMR (CDCl3, 300 MHz) δ 1.81-1.85 (m, 4H), 3.12-3.18 (m, 8H), 3.59 (s, 3H), 3.81 (m, 4H), 4.43 (s, 2H), 6.71 (d, 1H), 8.18 (d, 1H); MS (TS) 342 (MH+).

後処理

  1. washwashed twice with water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated to an oil which
  6. customwas purified by flash chromatography (95:5 dichloromethane:methanol)

出典と根拠

ORDレコード
ord-09fb55001e3945a1915a9bced150657f
出典データセット
uspto-grants-2005_08
特許番号
US06936600B2

関連ノート

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