Hydrochloric Acid → HCID 178464033, compound

HRID 424516Notes

Reaction equation

HRID 424516 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[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)[CH3:2].[ClH:26].CCOCC>CO>[ClH:26].[ClH:26].[CH2:24]([N:3]([CH2:1][CH3:2])[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)[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178464032HCID 178464032, compound

Product 1

HCID 178464033HCID 178464033, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(4-(2-(diethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)thiophene-2-carboximidamide (1.149 g, 3.07 mmol) in MeOH (5 mL) was added 1M HCl in ether (15.35 mL, 15.35 mmol) at room temperature. The mixture was stirred for 5 minutes under argon atmosphere and concentrated to give a yellow solid (1.37 g, quantitative). 1H NMR (DMSO-d6) δ 11.24 (s, 2H), 9.68 (s, 1H), 8.69 (s, 1H), 8.15-8.13 (m, 2H), 7.37-7.34 (m, 1H), 7.12-7.00 (m, 3H), 3.88-3.83 (m, 2H), 3.69-3.66 (m, 2H), 3.17-3.10 (m, 8H), 1.25 (t, J=7.2 Hz, 6H); ESI-MS (m/z, %): 377, 375 (MH+, free base, 58), 278, 276 (100); ESI-HRMS calculated for C19H25N4S2 (MH+, free base), calculated: 375.1671, observed: 375.1667; HPLC: 95% by area.

Workup

  1. concentrationconcentrated
  2. customto give a yellow solid (1.37 g, quantitative)

Sources & evidence

ORD record
ord-5ad2803668cc49929a9044a82770f8cb
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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