Hydrochloric Acid → HCID 178483716, compound

HRID 424533Notes

Reaction equation

HRID 424533 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[O:19][CH:20]=[CH:21][CH:22]=3)=[NH:17])[CH:13]=[CH:14][C:6]1=2.[ClH:24].CCOCC>CO>[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[O:19][CH:20]=[CH:21][CH:22]=3)=[NH:17])[CH:13]=[CH:14][C:6]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178483715HCID 178483715, compound

Product 1

HCID 178483716HCID 178483716, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(4-(2-(Dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)furan-2-carboximidamide (0.166 g, 0.504 mmol) was dissolved in MeOH (2 mL). 1M HCl in ether (2.52 mL, 2.52 mmol) was added to the solution at room temperature, and the reaction was stirred for 5 minutes under argon atmosphere. The mixture was concentrated to give a light yellow solid (0.18 g, 93%). 1H NMR (DMSO-d6) δ 11.36 (s, 1H), 11.25 (brs, 1H), 9.68 (s, 1H), 8.69 (s, 1H), 8.23 (s, 1H), 7.91 (d, J=2.7 Hz, 1H), 7.07-6.96 (m, 3H), 6.90 (d, J=1.8 Hz, 1H), 3.82-3.77 (m, 2H), 3.67-3.63 (m, 2H), 3.25-3.22 (m, 2H), 3.12-3.09 (m, 2H), 2.80 (s, 3H), 2.78 (s, 3H); ESI-MS (m/z, %): 333, 331 (MH+, free base, 100), 260, 262 (57); HRMS calculated for C17H23N4OS (MH+, free base): calculated: 331.1587, observed: 331.1589; HPLC purity: 98% by area.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-adbe9ca08d744a598ee25cca6dd95433
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

Loading…