Potassium Carbonate → HCID 66760356, compound

HRID 389508Notes

Reaction equation

HRID 389508 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:18]2[CH:19]=[N:20][N:21]([CH:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]3)[CH:22]=2)=[C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=3)[O:8][C:7]=12.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=1>CC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:18]2[CH:19]=[N:20][N:21]([CH:23]3[CH2:24][CH2:25][N:26]([C:29](=[O:31])[CH3:30])[CH2:27][CH2:28]3)[CH:22]=2)=[C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=4)[CH:12]=3)[O:8][C:7]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5642092-(Bromomethyl)pyridineHCID 66759532HCID 66759532, compound

Product 1

HCID 66760356HCID 66760356, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(4-{4-[7-Amino-2-(3-hydroxy-phenyl)-furo[2,3-c]pyridin-4-yl]-pyrazol-1-yl}-piperidin-1-yl)-ethanone (50 mg, 0.12 mmol) was dissolved in acetone (10 mL) and potassium carbonate (50 mg, 0.36 mmol) and 2-bromomethyl-pyridine (24 mg, 0.14 mmol) was added. The solution was stirred at RT overnight. After filtration the filtrate was concentrated and the residue was purified by preparative TLC (10% MeOH:DCM) to afford 8 mg (13%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.56-8.57 (d, J=4 Hz, 1H), 8.17 (s, 1H), 7.85-7.93 (m, 3H), 7.74 (s, 1H), 7.66-7.68 (d, J=7.2 Hz, 2H), 7.54 (s, 1H), 7.39-7.43 (m, 2H), 7.10-7.12 (d, J=8 Hz, 1H), 5.29 (s, 2H), 4.65-4.72 (m, 1H), 4.49-4.60 (m, 1H), 4.06-4.14 (m, 1H), 3.33-3.35 (m, 1H), 2.80-2.88 (m, 1H), 2.20-2.27 (m, 2H), 2.16 (s, 3H), 1.95-2.11 (m, 2H); MS (ESI): 509.11 [M+H]+; HPLC tR=2.18 min (ZQ3: polar—4 min).

Workup

  1. filtrationAfter filtration the filtrate
  2. concentrationwas concentrated
  3. customthe residue was purified by preparative TLC (10% MeOH:DCM)

Sources & evidence

ORD record
ord-24bc1155173a408ab68ac9cabd202407
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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