Triethylamine → HCID 178437920, compound

HRID 68730

Reaction equation

HRID 68730 reaction equation
Cl.[CH2:2]([C:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[N:8][C:7]=2[N:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:5]=1)[CH3:3].Cl.Br[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:2]([C:4]1[C:12]2[C:7](=[N:8][C:9]([CH:14]3[CH2:15][CH2:16][N:17]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:18][CH2:19]3)=[N:10][C:11]=2[OH:13])[N:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 881004-Bromopyridinium chlorideHCID 1363139973-ethyl-1-phenyl-6-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrochloride

Product 1

HCID 178437920HCID 178437920, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Into a 100-mL round-bottom flask, was placed a solution of 3-ethyl-1-phenyl-6-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrochloride (200 mg, 0.56 mmol, 1.00 equiv) in N,N-dimethylformamide (40 mL) at room temperature. To the resulting mixture was then added 4-bromopyridine hydrochloride (131 mg, 0.68 mmol, 1.10 equiv), in portions at room temperature, followed by triethylamine (188 mg, 1.86 mmol, 3.00 equiv), in portions at room temperature. The resulting solution was stirred overnight at 130° C. The resulting mixture was concentrated under vacuum. The resulting residue (150 mg) was purified by Prep-HPLC with the following conditions (Gilson Pre-HPLC): Column, SHISEIDO, CAPCELL PAK C18, 20 mm ID*250 mm, 5 u; mobile phase, methanol/H2O; Detector, UV 254 nm, to yield 3-ethyl-1-phenyl-6-(3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol as a white solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customat room temperature
  3. customat room temperature
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThe resulting residue (150 mg) was purified by Prep-HPLC with the following conditions (Gilson Pre-HPLC)

Sources & evidence

ORD record
ord-090954218796419793ebe79fef513f97
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Linked notes

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