Water → HCID 66920851, compound

HRID 1364578Notes

Reaction equation

HRID 1364578 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[O:14])[CH:3]=1.C(NC(C)C)(C)C.Br[CH2:32][C:33]([O:35]C(C)(C)C)=[O:34].O>CN(C)C=O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][CH2:32][C:33]([OH:35])=[O:34])=[CH:21][CH:22]=2)=[O:14])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 79177tert-Butyl bromoacetateHCID 66920631HCID 66920631, compound

Product 1

HCID 66920851HCID 66920851, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 115 (63 mg, 0.2 mmol) and N,N-diisopropylamine (40 μL, 0.22 mmol) in 0.5 mL of anhydrous N,N-dimethylformamide, was added tert-butyl bromoacetate (40 μL, 0.3 mmol). The resulting mixture was stirred at room temperature overnight, after which water was added, and the precipitate filtered. The solid was dissolved in 1 mL of trifluoroacetic acid, then stirred at room temperature for an additional hour. The mixture was concentrated, and purified via reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate) to give 35 mg (41%, 2 steps) of the titled compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (t, J=7.1 Hz, 3H), 3.46 (s, 2H), 4.30 (d, J=6.1 Hz, 2H), 4.46 (q, J=7.3 Hz, 2H), 6.46 (d, J=8.5 Hz, 2H), 7.02 (d, J=8.3 Hz, 2H), 7.07 (s, 1H), 7.28 (bs, 2H), 8.76 (t, J=6.2 Hz, 1H). MS (ESI+) m/e=370 (M+H)+.

Workup

  1. filtrationthe precipitate filtered
  2. dissolutionThe solid was dissolved in 1 mL of trifluoroacetic acid
  3. stirringstirred at room temperature for an additional hour
  4. concentrationThe mixture was concentrated
  5. custompurified via reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate)

Sources & evidence

ORD record
ord-70cd35a279b74253a7ad7879ba5a4cc9
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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