Triethylamine → HCID 66732380, compound

HRID 1966829Notes

Reaction equation

HRID 1966829 reaction equation
Cl.[CH:2]1([NH:8][C:9]2[C:10]3[CH:27]=[N:26][N:25]([CH2:28][CH3:29])[C:11]=3[N:12]=[CH:13][C:14]=2[C:15]2[CH2:19][C:18]3([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[O:17][N:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:37](Cl)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>ClCCl>[CH:2]1([NH:8][C:9]2[C:10]3[CH:27]=[N:26][N:25]([CH2:28][CH3:29])[C:11]=3[N:12]=[CH:13][C:14]=2[C:15]2[CH2:19][C:18]3([CH2:24][CH2:23][N:22]([C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:21][CH2:20]3)[O:17][N:16]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 66732657HCID 66732657, compound

Product 1

HCID 66732380HCID 66732380, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Cyclohexyl-1-ethyl-5-(1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine hydrochloride salt (70 mg, 0.00016 mole) (example 22) was taken in dichloromethane (10 ml). Triethyl amine (0.07 ml, 0.00050 mole) and pivaloyl chloride (0.030 ml, 0.00025 mole) were added at 0° C. The reaction mixture was stirred at room temperature overnight. It was diluted with dichloromethane, washed with sodium bicarbonate solution, extracted with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product obtained was purified by preparative thin layer chromatography.

Workup

  1. washwashed with sodium bicarbonate solution
  2. extractionextracted with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7597dacb6a56427ab0f48fe4f89cb790
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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