7-Amino-4-(2-(dimethylamino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one → HCID 178483725, compound

HRID 424473Notes

Reaction equation

HRID 424473 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[C:9](=[O:16])[CH2:8][O:7][C:6]=2[CH:17]=1.I.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](SC)=[NH:25]>C(O)C.C([O-])(O)=O.[Na+]>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][N:10]1[C:9](=[O:16])[CH2:8][O:7][C:6]2[CH:17]=[C:2]([NH:1][C:24]([C:20]3[S:19][CH:23]=[CH:22][CH:21]=3)=[NH:25])[CH:3]=[CH:4][C:5]1=2

Participants

5

Reactant 2

HCID 242533077-Amino-4-(2-(dimethylamino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide2×

Product 1

HCID 178483725HCID 178483725, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 7-amino-4-(2-(dimethylamino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (0.125 g, 0.531 mmol) in dry ethanol (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.3 g, 1.062 mmol) at room temperature and stirred overnight (18 hours). At this time, additional methyl thiophene-2-carbimidothioate hydroiodide (0.3 g, 1.062 mmol) was added, and stirring was continued for another 24 hours. The reaction was diluted with saturated NaHCO3 solution (20 mL), and the product was extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layers were washed with brine (15 mL) and dried (Na2SO4). The solvent was evaporated, and the crude material was purified by column chromatography (5:95 (2M NH3 in MeOH):CH2Cl2) to obtain the title compound 5 (0.16 g, 88%) as a solid. 1H NMR (DMSO-d6) δ 2.19 (s, 6H), 2.43 (t, 2H, J=6.9 Hz), 3.97 (t, 2H, J=6.9 Hz), 4.58 (s, 2H), 6.48-6.58 (m, 4H), 7.06-7.14 (m, 2H), 7.60 (d, 1H, J=5.1 Hz), 7.74 (d, 1H, J=3.3 Hz); ESI-MS (m/z, %): 345 (MH+, 100), 128 (85); ESI-HRMS calculated for C17H21N4O2S (MH+), calculated: 345.1379; observed: 345.1384; HPLC-purity: 93.15% by area.

Workup

  1. stirringstirring
  2. waitwas continued for another 24 hours
  3. extractionthe product was extracted into CH2Cl2 (2×20 mL)
  4. washThe combined CH2Cl2 layers were washed with brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. customthe crude material was purified by column chromatography (5:95 (2M NH3 in MeOH):CH2Cl2)

Sources & evidence

ORD record
ord-c511d634838e4ee0a64ff3173e15feb8
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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