Ethyl bromoacetate → HCID 21090621, compound

HRID 350962Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[S:11])=[N:6][CH:7]=1.[CH3:25][C:26]([O-])=[O:27].[Na+].BrCC(OCC)=O>C(O)C>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:9]2[C:26](=[O:27])[CH2:25][S:11][C:10]2=[N:12][C:13]2[CH:14]=[CH:15][C:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:17][CH:18]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 1-(5-Methylpyrazin-2-ylmethyl)-3-(4-morpholin-4-ylphenyl)-thiourea (1.7 g, 5.0 mmol, 1.0 equiv) and NaOAc (0.82 g, 10.0 mmol, 2.0 equiv) in 30 mL ethanol was treated with ethyl bromoacetate (0.55 ml, 5.0 mmol, 1.0 equiv) as a neat liquid via syringe. The heterogeneous mixture was heated to 80° C. overnight. The solvent was removed in vacuo, and the residue was partitioned between EtOAc and saturated NaHCO3. After drying the organic layer with brine and Na2SO4, the product was purified by flash chromatography (40 to 90% EtOAc in hexanes) to afford 1.4 g (73%) of the title compound as a yellow-orange foam: 1H NMR (500 MHz, CDCl3) δ 8.53 (d, 1H, J=1.5 Hz), 8.39 (d, 1H, J=1.5 Hz), 6.85 (s, 4H), 5.15 (s, 2H), 3.90 (s, 2H), 3.85 (m, 4H), 3.12 (m, 4H), 2.54 (s, 3H); MS (ESI) m/z=384.2 (MH+).

Workup

customThe solvent was removed in vacuo
customthe residue was partitioned between EtOAc and saturated NaHCO3
dry with materialAfter drying the organic layer with brine and Na2SO4
customthe product was purified by flash chromatography (40 to 90% EtOAc in hexanes)

Sources & evidence

ORD record: ord-3c644bfe255b4c0f85bfac4ee8dd983a
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183302B2

Reaction notes

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