A-769662 → HCID 135594051, compound

HRID 1244154Notes

Reaction equation

HRID 1244154 reaction equation
[CH3:1][Mg+].[Br-].[OH:4][C:5]1[C:6]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[OH:29])=[CH:19][CH:18]=3)=[CH:15][S:14][C:7]=2[NH:8][C:9](=[O:13])[C:10]=1[C:11]#[N:12]>C1COCC1>[C:11]([C:10]1[C:9](=[O:13])[NH:8][C:7]2[S:14][CH:15]=[C:16]([C:17]3[CH:18]=[CH:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[OH:29])=[CH:21][CH:22]=3)[C:6]=2[C:5]=1[OH:4])(=[NH:12])[CH3:1]

Participants

4

Reactant 2

HCID 54708532A-769662HCID 178418689HCID 178418689, compound

Product 1

HCID 135594051HCID 135594051, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeMgBr (1.4 M in ether, 15 mL, 21 mmol) was slowly added to a solution of 4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (1.5 g, 4.18 mmol) in anhydrous THF (90 mL) at 0° C. The reaction mixture was slowly warmed to room temperature over 4 hours and quenched with 1N HCl. It was then filtered, concentrated, and purified on a RP-HPLC system to give the title compound. MS (ESI) m/e 375.0 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 12.37 (br s, 1H), 11.33 (s, 1H), 9.51 (s, 1H), 9.32 (s, 1H), 7.49 (d, J=8.59, 2H), 7.42 (d, J=8.59, 2H), 7.29 (dd, J=7.68, 1.85, 1H), 7.18–7.14 (m, 1H), 6.96 (dd, J=8.29, 1.23, 1H), 6.91–6.84 (m, 1H), 6.75 (s, 1H), 2.55 (s, 3H).

Workup

  1. customquenched with 1N HCl
  2. filtrationIt was then filtered
  3. concentrationconcentrated
  4. custompurified on a RP-HPLC system

Sources & evidence

ORD record
ord-bc50fa8993154f99b86fc46fff533dde
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

Loading…