Hydrochloric Acid → HCID 178478757, compound

HRID 424592Notes

Reaction equation

HRID 424592 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([N:6]2[CH2:11][CH2:10][S:9][C:8]3[CH:12]=[C:13]([NH:16][C:17]([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)=[NH:18])[CH:14]=[CH:15][C:7]2=3)[CH2:2]1.[ClH:24].CCOCC>CO>[ClH:24].[ClH:24].[NH:1]1[CH2:5][CH2:4][CH:3]([N:6]2[CH2:11][CH2:10][S:9][C:8]3[CH:12]=[C:13]([NH:16][C:17]([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)=[NH:18])[CH:14]=[CH:15][C:7]2=3)[CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178511898HCID 178511898, compound

Product 1

HCID 178478757HCID 178478757, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(4-(Pyrrolidin-3-yl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)thiophene-2-carboximidamide (0.1264 g, 0.367 mmol) in MeOH (3 mL) was treated with 1M HCl in ether (1.835 mL, 1.835 mmol). The mixture was stirred at room temperature for 5 minutes and was concentrated to give a light yellow solid (0.16 g, quantitative). 1H NMR (DMSO-d6) δ 11.30 (s, 1H), 9.83 (brs, 1H), 9.70 (s, 1H), 9.57 (brs, 1H), 8.70 (s, 1H), 8.15-8.13 (m, 2H), 7.37-7.34 (m, 1H), 7.10-7.00 (m, 3H), 4.74-4.63 (m, 1H), 3.60-3.40 (m, 5H), 3.16-3.05 (m, 3H), 2.26-2.15 (m, 1H), 2.05-1.92 (m, 1H); ESI-MS (m/z, %): 347, 345 (MH+, freebase, 61), 278, 276 (100); HRMS (C17H21N4S2, MH+, freebase): calculated: 345.1202, observed: 345.1195. HPLC purity: 99% by area.

Workup

  1. concentrationwas concentrated
  2. customto give a light yellow solid (0.16 g, quantitative)

Sources & evidence

ORD record
ord-cb819e40ff7b437ea291ae10e00e1c81
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

Loading…