4-(2-(Dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine → HCID 178483715, compound

HRID 1917188Notes

Reaction equation

HRID 1917188 reaction equation
Br.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](SCC1C=CC=CC=1)=[NH:8].[CH3:17][N:18]([CH3:32])[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][S:24][C:23]2[CH:27]=[C:28]([NH2:31])[CH:29]=[CH:30][C:22]1=2>CCO>[CH3:17][N:18]([CH3:32])[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][S:24][C:23]2[CH:27]=[C:28]([NH:31][C:7]([C:3]3[O:2][CH:6]=[CH:5][CH:4]=3)=[NH:8])[CH:29]=[CH:30][C:22]1=2

Participants

4

Reactant 2

HCID 591441264-(2-(Dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amineHCID 66704617Benzyl furan-2-carbimidothioate hydrobromide

Product 1

HCID 178483715HCID 178483715, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl furan-2-carbimidothioate hydrobromide (1.139 g, 3.82 mmol) was added to a mixture of 4-(2-(dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (0.829 g, 3.49 mmol) in EtOH (20 mL). The mixture was stirred for 2 days under argon atmosphere. The solution was quenched with saturated sodium bicarbonate (50 mL). The solution was transferred to a separatory funnel, diluted with water (50 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 subjected to flash chromatography on silica gel (2.5-5% (2M NH3 in MeOH):CH2Cl2). The collected fractions gave compound 19 as a brown oil (1.03 g, 90%). 1H NMR (CDCl3) δ 7.46 (s, 1H), 7.03 (brs, 1H), 6.73-6.68 (m, 3H), 6.50 (brs, 1H), 5.03 (brs, 2H), 3.62-3.59 (m, 2H), 3.40 (t, J=7.2 Hz, 2H), 3.05-3.02 (m, 2H), 2.52 (t, J=7.5 Hz, 2H), 2.29 (s, 6H); ESI-MS (m/z, %): 333, 331 (MH+, 91), 260, 262 (100).

Workup

  1. customThe solution was quenched with saturated sodium bicarbonate (50 mL)
  2. customThe solution was transferred to a separatory funnel
  3. additiondiluted with water (50 mL)
  4. extractionextracted with CH2Cl2 (50 mL)
  5. washThe aqueous phase was washed with CH2Cl2 (50 mL)
  6. washThe combined organic fractions were washed with brine (50 mL)
  7. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-c69a008a613a40d4bac9a5d8d0e09ffa
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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