Hydrochloric Acid → HCID 178478756, compound

HRID 424569Notes

Reaction equation

HRID 424569 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][S:10][C:9]2[CH:13]=[CH:14][C:15]([NH:17][C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[NH:19])=[CH:16][C:8]1=2.[ClH:25]>CO>[ClH:25].[ClH:25].[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][S:10][C:9]2[CH:13]=[CH:14][C:15]([NH:17][C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[NH:19])=[CH:16][C:8]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178511894HCID 178511894, compound

Product 1

HCID 178478756HCID 178478756, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-(2-(2-hydroxyethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)thiophene-2-carboximidamide (165 mg, 0.455 mmol) in methanol (2 mL) was added HCl (1M in diethyl ether; 1.365 mL, 1.365 mmol). The resulting solution was concentrated, giving a yellow solid (197 mg, 99%). 1H NMR (DMSO-d6) δ 11.46 (s, 1H), 9.75 (s, 1H), 9.21-9.09 (m, 2H), 8.74 (s, 1H), 8.21-8.11 (m, 2H), 7.40-7.32 (m, 1H), 7.12 (d, J=8.1 Hz, 1H), 7.03 (s, 1H), 6.62 (d, J=7.8 Hz, 1H), 3.73-3.60 (m, 6H), 3.18-3.07 (m, 4H), 3.06-2.98 (m, 2H); HRMS (C17H23N4OS2, MH+, free base): calculated: 363.1307, observed: 363.1290. HPLC purity: 97% by area.

Workup

  1. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-a93c40c471b442fbb539d17faa8e695d
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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