HCID 21049003, compound → HCID 21048999, compound

HRID 2212393Notes

Reaction equation

HRID 2212393 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:16][CH2:15][CH:14]([NH:17][S:18]([N:21]3[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]3)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:35][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:12][CH2:13][CH:14]([NH:17][S:18]([N:21]3[CH2:25][CH2:24][C:23]([OH:26])([CH3:35])[CH2:22]3)(=[O:20])=[O:19])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21049003HCID 21049003, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21048999HCID 21048999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The product from Example 182 (65 mg, 0.12 mmol) in tetrahydrofuran (10 ml) at 0° C. was treated with methyl magnesium bromide (3M solution in tetrahydrofuran, 0.4 ml). The reaction was stirred at 0° C. for 45 minutes then quenched with NH4Cl solution, extracted into ethyl acetate and evaporated. The residue was purified by chromatography on silica (diethyl ether) to afford the desired compound (18 mg). 1H NMR (360 MHz, CDCl3) δ 7.38–7.31 (4H, m), 7.07–7.06 (2H, m) 6.89–6.80 (1H, m), 4.90–4.98 (1H, d, J=4 Hz), 3.58–3.55 (2H, m), 3.49–3.40 (2H, m), 3.24–3.23 (1H, m), 2.56–2.39 (4H, m), 2.12 (1H, s), 2.04–1.94 (4H, m), 1.52–1.46 (2H, m), 1.45 (3H, s). m/z=571, 573 [MNa]+

Workup

  1. customthen quenched with NH4Cl solution
  2. extractionextracted into ethyl acetate
  3. customevaporated
  4. customThe residue was purified by chromatography on silica (diethyl ether)

Sources & evidence

ORD record
ord-205576340a874f5093a11c38ad49f5a4
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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