Hydrogen Bromide → HCID 59022464, compound

HRID 597839Notes

Reaction equation

HRID 597839 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:17]4([CH2:21][CH2:20][N:19](C(OCC5C=CC=CC=5)=O)[CH2:18]4)[O:16][CH2:15][CH2:14][N:13]3[C:32](=[O:35])[C:33]=2[OH:34])=[O:9])=[C:4]([N:38]2[C:42]([CH3:43])=[N:41][CH:40]=[N:39]2)[CH:3]=1.Br.Br.CC(O)=O>O1CCOCC1.CC(O)=O>[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:17]4([CH2:21][CH2:20][NH:19][CH2:18]4)[O:16][CH2:15][CH2:14][N:13]3[C:32](=[O:35])[C:33]=2[OH:34])=[O:9])=[C:4]([N:38]2[C:42]([CH3:43])=[N:41][CH:40]=[N:39]2)[CH:3]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 54681978HCID 54681978, compound

Product 1

HCID 59022464HCID 59022464, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of Example 37 (1.1358 g, 1.9265 mmol) in 1,4-dioxane (10 mL) was added 33 wt % HBr in AcOH (2 mL) at room temperature. Immediately upon addition of HBr/AcOH to the reaction, solids precipitated out of the reaction mixture. So, 3 mL of anhydrous MeOH was added and stirred for 2 h. Then, the reaction mixture was purified by preparative HPLC using water/MeOH containing 0.1% TFA to afford desired product (0.448 g, 41%) as white solid. 1H NMR (500 MHz, DMSO-d6) δ: 1205 (1H, s), 9.35-9.28 (1H, br s), 9.27-9.19 (1H, br s), 9.14 (1H, t, J=6.1 Hz), 8.12 (1H, s), 7.57-7.53 (2H, m), 7.48-7.44 (1H, m), 4.27 (2H, d, J=6.1 Hz), 4.09-4.05 (2H, m), 3.91-3.86 (2H, m), 3.70-3.49 (3H, m), 3.42-3.34 (1H, m), 2.66-2.59 (1H, m), 2.45-2.39 (1H, m), 2.33 (3H, s). HRMS (M+H) calcd for C21H23N7O4F: 456.1796; found: 456.1805.

Workup

  1. customto the reaction, solids
  2. customprecipitated out of the reaction mixture
  3. additionSo, 3 mL of anhydrous MeOH was added
  4. customThen, the reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-710bf39d5f3b4ab2b200f70ff4d04709
Source dataset
uspto-grants-2011_03
Patent number
US07897593B2

Reaction notes

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