Benzyl Bromide → HCID 178420434, compound

HRID 968882Notes

Reaction equation

HRID 968882 reaction equation
[NH:1]([C:8]1[N:12]=[C:11]([SH:13])[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[NH:1]([C:8]1[N:12]=[C:11]([S:13][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178527885HCID 178527885, compound

Product 1

HCID 178420434HCID 178420434, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of the compound of Example 1 (c) (23 mg, 0.12 mmol) in 1.2 mL of DMF was added K2CO3 (17 mg, 0.12 mmol), followed by benzyl bromide (20 mg, 0.12 mmol). The mixture was stirred overnight, filtered, and purified by preparative HPLC to afford the title compound as a white solid (30 mg, 70%). 1H-NMR (400 MHz, d6-DMSO) δ9.30 (broad singlet, 1H), 7.47 (d, 2H, J=8.1 Hz), 7.39 (d, 2H, J=7.3 Hz), 7.31 (t, 2H, J=7.3 Hz), 7.23 (quartet, 3H, J=7.3 Hz), 6.82 (t, 1H, J=7.3 Hz), and 4.3 (s, 2H).

Workup

  1. filtrationfiltered
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-6bd510f9f27f418fa70805e275fd731d
Source dataset
uspto-grants-2007_12
Patent number
US07304082B2

Reaction notes

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