HCID 66992896, compound → HCID 44553898, compound

HRID 1254055Notes

Reaction equation

HRID 1254055 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[CH3:30][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:22]=[CH:23][C:24]([C:27]([OH:29])([CH3:30])[CH3:28])=[CH:25][CH:26]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 66992896HCID 66992896, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 44553898HCID 44553898, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the crude product of Step 1 in 1 mL of THF was added 0.1 mmol of MeMgBr (3M in ether) at −78° C. After stirring at 0° C. for 1 hr, the reaction was quenched with aqueous NH4Cl, and the product was extracted with EtOAc. The combined extracts were concentrated and the crude product was purified by reverse phase HPLC to afford the title compound. 1H NMR (500 MHz, (CDCl3): 8.04 (d, 2H), 7.68 (m, 2H), 7.54 (d, 2H), 7.53 (m, 3H), 7.26 (d, 2H), 7.06 (d, 2H), 3.67 (s, 3H), 1.61 (s, 6H). LCMS: m/z 435 (M+H)+.

Workup

  1. customthe reaction was quenched with aqueous NH4Cl
  2. extractionthe product was extracted with EtOAc
  3. concentrationThe combined extracts were concentrated
  4. customthe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-b80163eaca314824b80bbc6e2ebe6237
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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