Diisopropylethylamine → HCID 44193964, compound

HRID 2076017Notes

Reaction equation

HRID 2076017 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[S:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.Br.BrC1[C:26](=O)[CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[CH2:24][CH2:23][CH2:22]1.C([N:38]([CH2:42][CH3:43])C(C)C)(C)C>C(O)C>[CH2:42]([N:38]1[CH2:26][CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:24]2[N:18]=[C:16]([NH:15][C:5]3[CH:6]=[CH:7][C:8]([N:9]4[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[S:17][C:23]=2[CH2:22]1)[C:43]1[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67096250HCID 67096250, compoundHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 44193964HCID 44193964, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (100 mg, 0.38 mmol) and of crude 6-bromo-2-(2-chloro-phenyl)-cyclohexanone hydrobromide (163 mg, 0.36 mmol) in ethanol (5 mL) was heated to reflux under an atmosphere of nitrogen for 2 days. N,N-diisopropyl ethyl amine (49 mg, 0.38 mmol) was added and the reaction was heated to reflux over night. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was treated with dichloromethane/methanol/concentrated aqueous NH4OH solution (9:1:0.1 v/v/v). The precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by reversed preparative HPLC using acetonitril/water (0.1% formic acid) to yield the title compound (6 mg, 3%) as a yellow solid. MS ISP (m/e): 541.9/543.9 (100/35) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.60 (s, 1H), 7.37 (m, 2H), 7.26 (m, 5H), 7.09-7.18 (m, 4H), 6.82 (s, 1H), 6.66 (d, 1H), 4.70 (m, 1H), 3.74 (m, 3H), 3.60 (s, 3H), 3.19 (dd, 1H), 2.81 (dd, 1H), 2.28 (s, 2H).

Workup

  1. temperatureto reflux under an atmosphere of nitrogen for 2 days
  2. temperaturethe reaction was heated
  3. temperatureto reflux over night
  4. customwas evaporated under reduced pressure
  5. additionthe residue was treated with dichloromethane/methanol/concentrated aqueous NH4OH solution (9:1:0.1 v/v/v)
  6. filtrationThe precipitate was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by reversed preparative HPLC

Sources & evidence

ORD record
ord-6f32f3fcc8c940b7aa20a6aa4934686d
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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