Hydrochloric Acid → HCID 178478755, compound

HRID 424564Notes

Reaction equation

HRID 424564 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][S:11][C:10]3[CH:14]=[CH:15][C:16]([NH:18][C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[NH:20])=[CH:17][C:9]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:26]>CO>[ClH:26].[ClH:26].[N:1]1([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][S:11][C:10]3[CH:14]=[CH:15][C:16]([NH:18][C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[NH:20])=[CH:17][C:9]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178511893HCID 178511893, compound

Product 1

HCID 178478755HCID 178478755, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)thiophene-2-carboximidamide (424 mg, 1.138 mmol) in methanol (4 mL) was added hydrogen chloride (1 M in diethyl ether; 3.41 mL, 3.41 mmol). The resulting mixture was concentrated in vacuo, giving an orange solid (507 mg, 100%). 1H NMR (DMSO-d6) δ 11.60-11.40 (m, 2H), 9.75 (s, 1H), 8.78 (s, 1H), 8.22-8.10 (m, 2H), 7.36 (t, J=8.4 Hz, 1H), 7.15-7.05 (m, 2H), 6.64 (d, J=8.1 Hz, 1H), 3.80-3.71 (m, 2H), 3.70-3.61 (m, 2H), 3.58-3.45 (m, 2H), 3.43-3.30 (m, 2H), 3.16-3.07 (m, 2H), 3.06-2.95 (m, 2H), 2.05-1.92 (m, 2H), 1.90-1.79 (m, 2H); HRMS (C19H25N4S2, MH+, free base): calculated: 373.1515, observed: 373.1512. HPLC purity: 97% by area.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-2507d720e55d4daea4328230f6f4acc9
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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