HCID 59807136, compound → HCID 178483724, compound

HRID 1922409Notes

Reaction equation

HRID 1922409 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.I.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](SC)=[NH:26]>CCO.C([O-])([O-])=O.[Na+].[Na+]>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][N:8]1[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([NH:1][C:25]([C:21]3[S:20][CH:24]=[CH:23][CH:22]=3)=[NH:26])[C:7]1=2

Participants

5

Reactant 2

HCID 59807136HCID 59807136, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178483724HCID 178483724, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred solution of 9-amino-1-(2-(dimethylamino)ethyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (85 mg, 0.344 mmol) in EtOH (6 mL) was added methyl thiophene-2-carbimidothioate hydroiodide (196 mg, 0.687 mmol). The resulting suspension was stirred overnight at room temperature. The reaction mixture was then diluted with Na2CO3 (aq, sat) and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed in 2-5% 2M NH3/MeOH in dichloromethane, giving the desired product. Yield: 87 mg, 71%. 1H NMR (DMSO-d6) δ 7.75 (d, 1H, J=3.3 Hz, 7.61 (d, 1H, J=4.5 Hz), 7.16 (d, 1H, J=7.8 Hz), 7.10 (m, 1H), 6.82 (s, 1H), 6.66 (d, 1H, J=8.1 Hz), 6.46 (brs, 2H), 2.65 (m, 3H), 2.28 (m, 3H), 2.17 (m, 2H), 1.9-2.15 (m, 8H). ESI-MS (m/z, %): 357 (MH+, 100), 312 (48), 156 (38), 148 (31).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. customThe combined organics were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed in 2-5% 2M NH3/MeOH in dichloromethane

Sources & evidence

ORD record
ord-57600a8c56db4f63b0b3b6377b5e9df5
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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