4-(2-(Pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine → HCID 178511900, compound

HRID 424502Notes

Reaction equation

HRID 424502 reaction equation
I.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](SC)=[NH:8].[N:11]1([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][S:21][C:20]3[CH:24]=[C:25]([NH2:28])[CH:26]=[CH:27][C:19]2=3)[CH2:15][CH2:14][CH2:13][CH2:12]1>CCO>[N:11]1([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][S:21][C:20]3[CH:24]=[C:25]([NH:28][C:7]([C:3]4[S:2][CH:6]=[CH:5][CH:4]=4)=[NH:8])[CH:26]=[CH:27][C:19]2=3)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 591441634-(2-(Pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511900HCID 178511900, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl thiophene-2-carbimidothioate hydroiodide (1.239 g, 4.34 mmol) was added to a mixture of 4-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (0.572 g, 2.172 mmol) in EtOH (20 mL). The reaction was stirred overnight at room temperature. The reaction was quenched with saturated sodium bicarbonate solution (30 mL). The mixture was then extracted with CH2Cl2 (50 mL), and 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 then 5% (2M NH3 MeOH)/CH2Cl2). The collected fractions gave compound 11 as light brown viscous liquid (0.71 g, 88%). 1H NMR (DMSO-d6) δ 7.69 (d, J=3.6 Hz, 1H), 7.56 (d, J=5.1 Hz, 1H), 7.08-7.06 (m, 1H), 6.67 (t, J=8.7 Hz, 1H), 6.50 (d, J=8.4 Hz, 1H), 6.46 (s, 1H), 6.32 (brs, 2H), 3.57-3.53 (m, 2H), 3.39-3.34 (m, 2H), 3.03-3.00 (m, 2H), 2.60 (t, J=7.2 Hz, 2H), 2.50 (brs, 4H), 1.68 (brs, 4H); ESI-MS (m/z, %): 375, 373 (MH+, 47), 278, 276 (100), 98 (21).

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution (30 mL)
  2. extractionThe mixture was then extracted 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)

Sources & evidence

ORD record
ord-8aa27334aeff440cbe2c2db3d7093f30
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

Loading…