Hydrochloric Acid → HCID 178483517, compound

HRID 424546Notes

Reaction equation

HRID 424546 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][S:9][C:8]2[CH:12]=[C:13]([NH:16][C:17]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[NH:18])[CH:14]=[CH:15][C:7]1=2.[ClH:25]>CO>[ClH:25].[ClH:25].[CH3:24][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][S:9][C:8]2[CH:12]=[C:13]([NH:16][C:17]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[NH:18])[CH:14]=[CH:15][C:7]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178483516HCID 178483516, compound

Product 1

HCID 178483517HCID 178483517, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(4-(3-(dimethylamino)propyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)thiophene-2-carboximidamide (0.16 g, 0.444 mmol) in dry methanol (5 mL) was treated with hydrogen chloride (1M solution in ether; 1.331 mL, 1.331 mmol) at room temperature. The mixture was stirred for 15 minutes, the solvent was evaporated, and the residue was dried under high vacuum to obtain the title product (0.19 g, 99%) as a solid. 1H NMR (DMSO-d6) δ 11.22 (s, 1H), 10.91 (brs, 1H), 9.67 (s, 1H), 8.69 (s, 1H), 8.15-8.11 (m, 2H), 7.36 (t, 1H, J=4.5 Hz), 7.04-6.88 (m, 3H), 3.64-3.61 (m, 2H), 3.41 (t, 2H, J=6.9 Hz), 3.14-3.02 (m, 4H), 2.72 (d, 6H, J=4.8 Hz), 2.06-1.98 (m, 2H); ESI-MS (m/z, %): 361 (MH+, free base, 91), 276 (100); ESI-HRMS calculated for C18H25N4S2 (MH+, free base), calculated: 361.1515, observed: 361.1515; HPLC purity: 98.15% by area.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-21295280421b4a39ad1c3085cbbbd625
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

Loading…