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

HRID 431661

반응식

HRID 431661 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-382525b63f2b4cbb99765ba3c815bbe1
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660740B1

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