Triethylamine → 3-[4-(4-Azidobut-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

HRID 1244164Notes

Reaction equation

HRID 1244164 reaction equation
[OH:1][C:2]1[C:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]#[C:21][CH2:22][CH2:23]O)=[CH:16][CH:15]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:37]=[N+:38]=[N-:39].[Na+]>CN(C=O)C>[N:37]([CH2:23][CH2:22][C:21]#[C:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[C:3]3[C:2]([OH:1])=[C:7]([C:8]#[N:9])[C:6](=[O:10])[NH:5][C:4]=3[S:11][CH:12]=2)=[CH:15][CH:16]=1)=[N+:38]=[N-:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 546898814-Hydroxy-3-[4-(4-hydroxybut-1-ynyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 546898823-[4-(4-Azidobut-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-3-[4-(4-hydroxy-but-1-ynyl)-phenyl]-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (0.23 g, 0.7 mmol) in 5 mL DMF was added triethylamine (0.28 mL, 2 mmol), followed by MsCl (85 μL, 1 mmol). The mixture was stirred at rt for 2 hr, after which NaN3 (0.36 g, 5.6 mmol) was added, and heated to 90° C. overnight. Solvent was removed in vacuo and purified via reverse phase HPLC to afford the titled compound. MS (ESI) m/e 360 (M−H)+; 1H NMR (300 MHz, DMSO-d6): δ 2.76 (t, J=6.61 Hz, 2H), 3.52 (t, J=6.44 Hz, 2H), 6.67 (s, 1H), 7.29 (d, J=8.48 Hz, 2H), 7.44 (d, J=8.48 Hz, 2H).

Workup

  1. temperatureheated to 90° C. overnight
  2. customSolvent was removed in vacuo
  3. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-88e59fc15dd747ba95815d0a13092ef6
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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