Hydrochloric Acid → Gkt-136901

HRID 1429865노트

반응식

HRID 1429865 반응식
[Na].C[O:3][C:4](=O)[CH2:5][C:6]1=[N:7][N:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:9](=[O:21])/[C:10]/1=[C:11](/[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)\[CH3:12].Cl>CC(O)C>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:8]1[C:9](=[O:21])[C:10]2=[C:11]([CH3:12])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:4](=[O:3])[CH:5]=[C:6]2[NH:7]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 178499640HCID 178499640, 화합물

생성물 1

HCID 17027464Gkt-136901수율 82%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

An isopropanolic solution of i-PrONa, obtained by dissolving of sodium (0.082 g, 3.57 mmol, 1 equiv) in i-PrOH (75 ml), was treated with methyl[(4E)-1-(2-chlorophenyl)-5-oxo-4-{1-[(pyridin-2-ylmethyl)amino]ethylidene}-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VIII) (1.42 g, 3.57 mmol, 1 equiv.). The reaction mixture was refluxed for 1 h, then cooled and neutralized to pH 7 by addition of 0.59 ml of a 20% aqueous HCl solution. 50 ml of i-PrOH were removed in vacuo and 25 ml of H2O were added before placing the flask in the fridge overnight. The white precipitate formed was filtered off, washed with water (2×5 ml), then with cyclohexane and dried in vacuo. 1.07 g of pure product 2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione was obtained. Yield 82%. 1H-NMR: (500 MHz, DMSO-d6, ppm): 2.78 (s, 3H), 5.41 (s, 2H), 5.66 (s, 1H), 7.31-7.28 (m, 1H), 7.32 (d, J 7.9 Hz, 1H), 7.50-7.47 (m, 2H), 7.60-7.56 (m, 1H), 7.66-7.64 (m, 1H), 7.79 (td, J 7.6, 1.9 Hz, 1H), 8.48 (m, 1H), 10.73 (s, br, 1H). MS (ESI+): 367.9; MS (ESI−): 365.7.

후처리

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. temperaturecooled
  3. custom50 ml of i-PrOH were removed in vacuo and 25 ml of H2O
  4. additionwere added
  5. customin the fridge overnight
  6. customThe white precipitate formed
  7. filtrationwas filtered off
  8. washwashed with water (2×5 ml)
  9. dry with materialwith cyclohexane and dried in vacuo

출처 및 근거

ORD 기록
ord-0126cf7aa8364fb2879d7126a417aff4
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940760B2

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