4-(2-(1-Methylpyrrolidin-2-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine → HCID 178480164, compound

HRID 1917165Notes

Reaction equation

HRID 1917165 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12][C:11]2[CH:15]=[C:16]([NH2:19])[CH:17]=[CH:18][C:10]1=2.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27]>C(O)C>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12][C:11]2[CH:15]=[C:16]([NH:19][C:26]([C:22]3[S:21][CH:25]=[CH:24][CH:23]=3)=[NH:27])[CH:17]=[CH:18][C:10]1=2

Participants

4

Reactant 2

HCID 591441084-(2-(1-Methylpyrrolidin-2-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178480164HCID 178480164, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-(2-(1-methylpyrrolidin-2-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (0.7 g, 2.52 mmol) and methyl thiophene-2-carbimidothioate hydroiodide (1.439 g, 5.05 mmol) in dry ethanol (15 mL) was stirred at room temperature overnight (16 hours) under an argon atmosphere. At this time, the solvent was evaporated, and the residue was partitioned between saturated NaHCO3 solution (50 mL) and dichloromethane (25 mL). The mixture was transferred to a separatory funnel, and the organic layer was removed. The aqueous layer was extracted into dichloromethane (2×25 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was subjected to column chromatography on silica gel (sequence of eluents: 2:98 methanol:dichloromethane, 5:95 methanol:dichloromethane, and 5:95 (2M ammonia in methanol):dichloromethane) to give compound 13 as yellow syrup (0.48 g, 49%). 1H-NMR (DMSO-d6) δ 7.69 (brd, J=2.7 Hz, 1H), 7.57 (brd, J=4.5 Hz, 1H), 7.07 (dd, J=3.9, 4.8 Hz, 1H), 6.52 (dd, J=1.8, 8.1 Hz, 2H), 6.47 (brd, J=1.8 Hz, 1H), 6.38 (brs, 2H), 3.51-3.47 (m, 2H), 3.28-3.22 (m, 2H), 3.05-3.02 (m, 2H), 2.99-2.93 (m, 1H), 2.24 (s, 3H), 2.12-2.06 (m, 2H), 1.94-1.87 (m, 2H), 1.68-1.63 (m, 2H), 1.51-1.42 (m, 2H); ESI-MS (m/z, %): 387 (MH+, 90), 276 (100), 194 (50).

Workup

  1. customAt this time, the solvent was evaporated
  2. customthe residue was partitioned between saturated NaHCO3 solution (50 mL) and dichloromethane (25 mL)
  3. customThe mixture was transferred to a separatory funnel
  4. customthe organic layer was removed
  5. extractionThe aqueous layer was extracted into dichloromethane (2×25 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1a24f93390d84b40aac2eb46ce3544b5
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

Loading…