Benzyl Bromide → HCID 59753810, compound

HRID 1453690Notes

Reaction equation

HRID 1453690 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[S:13](=[O:21])(=[O:20])[NH:12][N:11]=2)=[CH:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Br[CH2:37][C:38]([O:40]C(C)(C)C)=[O:39]>CN(C=O)C>[CH2:28]([N:12]1[N:11]=[C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:1]([CH2:37][C:38]([OH:40])=[O:39])[CH:2]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[S:13]1(=[O:21])=[O:20])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium Carbonate2×HCID 79177tert-Butyl bromoacetateHCID 136388609HCID 136388609, compound

Product 1

HCID 59753810HCID 59753810, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

The product of step c) (93 mg, 0.3 mmol) was dissolved in 3 mL DMF and treated with K2CO3 (50 mg, 0.36 mmol) and benzyl bromide (57 mg, 0.33 mmol). After stirring at 75° C. overnight, t-butyl bromoacetate (0.36 mmol, 70 mg) and was added along with an additional quantity of K2CO3 (0.39 mmol, 54 mg). The reaction was heated for an additional 2 hours. The crude reaction was partitioned between EtOAc and water. The organic layer was concentrated to dryness and treated with TFA (3 mL). After 1 h, the reaction was concentrated and purified by preparative LCMS to give the title compound. 1H NMR (DMSO-d6) δ 8.15 (d, 1H, J=3.6 Hz), 8.07-7.94 (m, 3H), 7.92 (s, 1H), 7.59 (d, J=7.5 Hz, 1H), 7.51-7.31 (m, 6H), 7.22 (t, J=7.2 Hz, 1H), 7.04 (t, J=7.8 Hz, 1H), 5.12 (s, 2H), 5.07 (s, 2H); MS: ESI (negative): 444 (M−H).

Workup

  1. temperatureThe reaction was heated for an additional 2 hours
  2. customThe crude reaction
  3. customwas partitioned between EtOAc and water
  4. concentrationThe organic layer was concentrated to dryness
  5. additiontreated with TFA (3 mL)
  6. waitAfter 1 h
  7. concentrationthe reaction was concentrated
  8. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-b30456e858fd4c948fa56e3aa53911d1
Source dataset
uspto-grants-2009_01
Patent number
US07476667B2

Reaction notes

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