N-Methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine → Tofacitinib

HRID 1594375노트

반응식

HRID 1594375 반응식
[CH3:1][N:2]([C@@H:12]1[C@H:17]([CH3:18])[CH2:16][CH2:15][NH:14][CH2:13]1)[C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.O=C1CCC(=O)N1[O:26][C:27](=O)[CH2:28][C:29]#[N:30]>C(O)C>[CH3:18][C@@H:17]1[CH2:16][CH2:15][N:14]([C:27](=[O:26])[CH2:28][C:29]#[N:30])[CH2:13][C@@H:12]1[N:2]([CH3:1])[C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1

참가 물질

4

반응물 2

HCID 23401507N-Methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 534158962,5-Dioxopyrrolidin-1-yl 2-cyanoacetate

생성물 1

HCID 9926791Tofacitinib수율 86.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of the product from Method B (1.0 g) dissolved in 30 mL of ethanol was added 0.82 g of cyano-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester and the resulting mixture stirred at room temperature for 2 h. The reaction mixture was filtered through Celite® and concentrated in vacuo. The residue was redissolved in dichloromethane, washed with saturated, aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated to dryness in vacuo affording 1.1 g (86%) of the title compound as a yellow foam. LRMS: 313 (M+1).

후처리

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washwashed with saturated, aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-fab41313f5474ba3a29c20fae2961a36
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07301023B2

반응 노트

불러오는 중…