Hydrochloric Acid → HCID 178484227, compound

HRID 1917194Notes

Reaction equation

HRID 1917194 reaction equation
[CH3:1][NH:2][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:23].CCOCC>CO>[ClH:23].[ClH:23].[CH3:1][NH:2][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 178484226HCID 178484226, compound

Product 1

HCID 178484227HCID 178484227, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(4-(2-(methylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)furan-2-carboximidamide (0.4353 g, 1.376 mmol) was dissolved in MeOH (3 mL). 1M HCl in ether (6.88 mL, 6.88 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 yellow solid (0.59 g, quantitative). 1H NMR (DMSO-d6) δ 11.31 (s, 1H), 9.58 (s, 1H), 9.30 (brs, 2H), 8.82 (s, 1H), 8.57 (s, 1H), 7.98 (s, 1H), 7.30 (d, J=1.2 Hz, 1H), 7.06-7.03 (m, 2H), 6.97 (dd, J=2.4, 8.7 Hz, 1H), 3.74-3.63 (m, 4H), 3.13-3.05 (m, 4H), 2.58-2.55 (m, 3H); ESI-MS (m/z, %): 319, 317 (MH+, free base, 100), 260 (98); HRMS calculated for C16H20N4OS (MH+, free base), calculated: 317.1430, observed: 317.1417; HPLC purity: 99% by area.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a yellow solid (0.59 g, quantitative)

Sources & evidence

ORD record
ord-3ff2f25d71f04a6e987e0b653149c807
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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