Hydrochloric Acid → HCID 178478759, compound

HRID 424513Notes

Reaction equation

HRID 424513 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][S:12][C:11]3[CH:15]=[C:16]([NH:19][C:20]([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)=[NH:21])[CH:17]=[CH:18][C:10]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:27]>CO>[ClH:27].[ClH:27].[N:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][S:12][C:11]3[CH:15]=[C:16]([NH:19][C:20]([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)=[NH:21])[CH:17]=[CH:18][C:10]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178511901HCID 178511901, compound

Product 1

HCID 178478759HCID 178478759, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(4-(2-(piperidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)thiophene-2-carboximidamide (0.288 g, 0.745 mmol) in anhydrous methanol (8 mL) was treated with hydrochloric acid (1M in ether; 3.72 mL, 3.72 mmol). The reaction was stirred at room temperature for 0.5 hours and then concentrated to give an orange solid (0.34 g, 99%). 1H-NMR (DMSO-d6) δ 11.21 (brs, 1H), 11.16 (brs, 1H), 9.67 (brs, 1H), 8.69 (brs, 1H), 8.15 (brd, J=4.8 Hz, 1H), 8.11 (brd, J=3.0 Hz, 1H), 7.38-7.35 (m, 1H), 7.11-6.98 (m, 3H), 3.89-3.84 (m, 2H), 3.68-3.64 (m, 2H), 3.45-3.42 (m, 2H), 3.22-3.15 (m, 2H), 3.12-3.09 (m, 2H), 2.89-2.88 (m, 2H), 1.87-1.71 (m, 5H), 1.42-1.38 (m, 1H); ESI-MS (m/z, %): 387 (MH+, free base, 100), 194 (23); ESI-HRMS calculated for C20H27N4S2 (MH+, free base): 387.1671, observed: 337.1657; HPLC purity: 99% by area.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-4c33e3a7a716495d8fe3af8c5667887a
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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