Hydrochloric Acid → HCID 178483719, compound

HRID 1917162Notes

Reaction equation

HRID 1917162 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([NH:15][C:16]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)=[NH:17])[CH:13]=[CH:14][C:6]1=2.[ClH:24]>C(O)C>[ClH:24].[ClH:24].[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([NH:15][C:16]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)=[NH:17])[CH:13]=[CH:14][C:6]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178483717HCID 178483717, compound

Product 1

HCID 178483719HCID 178483719, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-(2-(dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)thiophene-2-carboximidamide (0.44 g, 1.270 mmol) in dry ethanol (10 mL) was treated with hydrochloric acid (1M in ether; 6.35 mL, 6.35 mmol) and stirred at room temperature for 1 hour. The precipitate was isolated and washed with ether to give a yellow-green powder. The powder was dried under reduced pressure. (0.46 g, 86%). 1H-NMR (DMSO-d6) δ 11.25 (brs, 2H), 9.69 (brs, 1H), 8.69 (brs, 1H), 8.15-8.13 (m, 2H), 7.37-7.37 (m, 1H), 7.07-7.01 (m, 3H), 3.82-3.77 (m, 2H), 3.70-3.60 (m, 2H), 3.25-3.21 (m, 2H), 3.15-3.10 (m, 2H), 2.80 (d, J=3.6 Hz, 6H); ESI-MS (m/z, %): 347 (MH+, free base, 100); ESI-HRMS calculated for C17H23N4S2 (MH+, free base): 347.1358, observed: 347.1343; HPLC purity: 97% by area.

Workup

  1. customThe precipitate was isolated
  2. washwashed with ether
  3. customto give a yellow-green powder
  4. customThe powder was dried under reduced pressure

Sources & evidence

ORD record
ord-315b619a049847ffa96b6980d21c4efa
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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