N-Bromosuccinamide → HCID 54689823, compound

HRID 1244133Notes

Reaction equation

HRID 1244133 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][CH2:24][OH:25])=[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].[Br:26]NC(=O)CCC(N)=O>C(O)(=O)C>[Br:26][C:12]1[S:11][C:4]2[NH:5][C:6](=[O:10])[C:7]([C:8]#[N:9])=[C:2]([OH:1])[C:3]=2[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][OH:25])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 54689878HCID 54689878, compound

Product 1

HCID 54689823HCID 54689823, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 4-hydroxy-3-[4-(5-hydroxy-pent-1-ynyl)-phenyl]-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (35 mg, 0.1 mmol) in acetic acid (1 mL) was added N-bromosuccinamide (18 mg, 0.1 mmol) in a single portion at room temperature, and stirred at rt overnight. The reaction mixture was concentrated and purified by reverse phase HPLC to afford the titled compound. MS (ESI) m/e 428 (M−H)+; 1H NMR (300 MHz, DMSO-d6): δ 1.68–1.75 (m, 2H), 3.51–3.57 (m, 2H), 4.54 (t, J=5.26 Hz, 2H), 7.19 (d, J=8.48 Hz, 2H), 7.31 (d, J=8.48 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-7b380093ed08488a9e07c28aea83f5c6
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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