Triethylamine → HCID 135886518, compound

HRID 2424826Notes

Reaction equation

HRID 2424826 reaction equation
Cl.[CH2:2]([C@@H:4]1[CH2:8][NH:7][CH2:6][C@H:5]1[C:9]1[NH:10][C:11](=[O:24])[C:12]2[CH:17]=[N:16][N:15]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:13]=2[N:14]=1)[CH3:3].C(N(CC)CC)C.[N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=[CH:34][C:33]=1[C:42](Cl)=[O:43]>ClCCl>[CH2:2]([C@@H:4]1[CH2:8][N:7]([C:42]([C:33]2[CH:34]=[N:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:32]=2)=[O:43])[CH2:6][C@H:5]1[C:9]1[NH:10][C:11](=[O:24])[C:12]2[CH:17]=[N:16][N:15]([CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:13]=2[N:14]=1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734681Quinoxaline-2-carbonyl chlorideHCID 1363442016-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride

Product 1

HCID 135886518HCID 135886518, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride (73 mg) in dicloromethane (2 mL) was added triethylamine (62 mg) and 2-quinoxaloylchloride (40 mg) at 0° C. The reaction mixture was warmed to ambient temperature and stirred for 18 h. The reaction mixture was quenched with saturated sodium bicarbonate, extracted with methylene chloride, dried with magnesium sulfate, filtered and concentrated. Purification via CombiFlash flash chromatography eluting with 24% MeOH/methylene chloride provided the title compound. 400 MHz 1H NMR (CDCl3) δ 12.78-12.62 (m, 1H), 9.41 (d, J=7.5, Hz, 1H), 8.18-8.00 (m, 3H), 7.87-7.73 (m, 2H), 4.84-4.81 (m, 1H), 4.55-3.86 (m, 6H), 3.61-3.53 (m, 2H), 3.38-3.31 (m, 1H), 2.75 (m, 1H), 2.39-2.34 (m, 2H), 1.93-1.89 (m, 2H), 1.58-1.56 (m, 1H), 1.63-1.50 (m, 1H), 1.01-0.88 (m, 3H). MS: (M+H m/z 474.2).

Workup

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via CombiFlash flash chromatography
  7. washeluting with 24% MeOH/methylene chloride

Sources & evidence

ORD record
ord-07159f8bf0ab436b810913603813c4d8
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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