Diethylamine → HCID 54689831, compound

HRID 1244129Notes

Reaction equation

HRID 1244129 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:15]([OH:17])=[C:14]([C:18]#[N:19])[C:13](=[O:20])[NH:12][C:11]=3[S:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(NCC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45]([OH:53])(=[O:52])[CH2:46][CH2:47][CH2:48][CH2:49][C:50]#[CH:51]>CN(C=O)C.[Cu]I>[C:18]([C:14]1[C:13](=[O:20])[NH:12][C:11]2[S:10][CH:9]=[C:8]([C:4]3[CH:3]=[C:2]([C:51]#[C:50][CH2:49][CH2:48][CH2:47][CH2:46][C:45]([OH:53])=[O:52])[CH:7]=[CH:6][CH:5]=3)[C:16]=2[C:15]=1[OH:17])#[N:19]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 43779506-Heptynoic acidHCID 54691518HCID 54691518, compound

Product 1

HCID 54689831HCID 54689831, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-bromo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (50 mg, 0.15 mmol) in 1.5 mL DMF was added diethylamine (0.16 mL, 1.5 mmol), followed by copper(I) iodide (trace), Pd(PPh3)Cl2 (3.5 mg, 0.005 mmol), and triphenylphosphine (12 mg, 0.04 mmol). The resulting mixture was stirred at rt for 5 min, after which hept-6-ynoic acid (63 μL, 0.5 mmol) was added. The reaction was then heated to 120° C. using microwave reactor for 25 min, filtered, concentrated and purified by reverse phase HPLC to give the titled compound. MS (ESI) m/e 391 (M−H)+; 1H NMR (300 MHz, DMSO-d6): δ 1.54 (m, 4H), 2.22 (m, 4H), 6.68 (s, 1H), 7.21–7.26 (m, 2H), 7.37–7.44 (m, 2H).

Workup

  1. temperatureThe reaction was then heated to 120° C.
  2. customfor 25 min
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-6ae320663a1d43ff84953eaa2c8405d8
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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