Hydrochloric Acid → HCID 178483714, compound

HRID 424572Notes

Reaction equation

HRID 424572 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]=[CH:12][C:13]([NH:15][C:16]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)=[NH:17])=[CH:14][C:6]1=2.[ClH:24]>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]=[CH:12][C:13]([NH:15][C:16]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)=[NH:17])=[CH:14][C:6]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178483713N-(4-(2-(dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)thiophene-2-carboximidamide

Product 1

HCID 178483714HCID 178483714, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-(2-(dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)thiophene-2-carboximidamide (57 mg, 0.164 mmol) in methanol (2 mL) was added hydrogen chloride (1 M in diethyl ether; 0.493 mL, 0.493 mmol). The resulting mixture was then concentrated in vacuo to give a yellow-orange solid (68 mg, 99%). 1H NMR (DMSO-d6) δ 11.49 (s, 1H), 11.09 (brs, 1H), 9.74 (s, 1H), 8.78 (s, 1H), 8.19-8.12 (m, 2H), 7.39-7.33 (m, 1H), 7.15-7.05 (m, 2H), 6.66-6.60 (m, 1H), 3.79-3.70 (m, 2H), 3.70-3.60 (m, 2H), 3.32-3.21 (m, 2H), 3.16-3.08 (m, 2H), 2.81-2.74 (m, 6H); HRMS (C17H23N4S2, MH+, free base): calculated: 347.1358, observed: 347.1349. HPLC purity: 95% by area.

Workup

  1. concentrationThe resulting mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-24bf6ab3366f4d3b88fd9d5279ca93c3
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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