HCID 59144174, compound → HCID 178464032, compound

HRID 424515Notes

Reaction equation

HRID 424515 reaction equation
I.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](SC)=[NH:8].[CH2:11]([N:13]([CH2:27][CH3:28])[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][S:19][C:18]2[CH:22]=[C:23]([NH2:26])[CH:24]=[CH:25][C:17]1=2)[CH3:12]>CCO>[CH2:27]([N:13]([CH2:11][CH3:12])[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][S:19][C:18]2[CH:22]=[C:23]([NH:26][C:7]([C:3]3[S:2][CH:6]=[CH:5][CH:4]=3)=[NH:8])[CH:24]=[CH:25][C:17]1=2)[CH3:28]

Participants

4

Reactant 2

HCID 59144174HCID 59144174, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178464032HCID 178464032, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl thiophene-2-carbimidothioate hydroiodide (2.266 g, 7.94 mmol) was added to a mixture of 4-(2-(diethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (1.054 g, 3.97 mmol) in EtOH (20 mL). The mixture was stirred for 2 days at room temperature. The reaction was quenched with saturated sodium bicarbonate solution (30 mL) and extracted with CH2Cl2 (50 mL). The aqueous phase was washed with CH2Cl2 (50 mL). The combined organic fractions were washed with brine (50 mL) and dried (Na2SO4). The crude material was subject to flash chromatography on silica gel (CH2Cl2 followed by 3.5% (2M NH3 in MeOH):CH2Cl2). The collected fractions were concentrated, and the sample was subjected again to flash chromatography on silica gel (2.5% MeOH:CH2Cl2). The collected fractions were concentrated to give compound 15 as a brown solid. (1.23 g, 83%). 1H NMR (CDCl3) δ 7.40-7.36 (m, 2H), 7.05 (dd, J=3.9, 4.8 Hz, 1H), 6.73 (m, 3H), 3.65-3.61 (m, 1H), 3.39 (t, J=7.2 Hz, 2H), 3.05-3.02 (m, 2H), 2.67-2.54 (m, 6H), 1.04 (t, J=7.2 Hz, 6H); ESI-MS (m/z, %): 377, 375 (MH+, 35), 278, 276 (100).

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution (30 mL)
  2. extractionextracted with CH2Cl2 (50 mL)
  3. washThe aqueous phase was washed with CH2Cl2 (50 mL)
  4. washThe combined organic fractions were washed with brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationThe collected fractions were concentrated
  7. concentrationThe collected fractions were concentrated

Sources & evidence

ORD record
ord-155a4161cb8a494db2dfa361e77338d9
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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