Hydrochloric Acid → HCID 178480165, compound

HRID 424509Notes

Reaction equation

HRID 424509 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12][C:11]2[CH:15]=[C:16]([NH:19][C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[NH:21])[CH:17]=[CH:18][C:10]1=2.[ClH:27]>C(O)C>[ClH:27].[ClH:27].[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12][C:11]2[CH:15]=[C:16]([NH:19][C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[NH:21])[CH:17]=[CH:18][C:10]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178480164HCID 178480164, compound

Product 1

HCID 178480165HCID 178480165, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-(2-(1-methylpyrrolidin-2-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)thiophene-2-carboximidamide (0.48 g, 1.242 mmol) in dry ethanol (10 mL) was treated with hydrochloric acid (1M in ether; 6.21 mL, 6.21 mmol) and stirred for half an hour. The precipitate was collected and rinsed with ether. The precipitate was dissolved in methanol and concentrated to give a yellow-orange crystalline solid (0.57 g, 100%). 1H-NMR (DMSO-d6) δ 11.22 (brs, 1H), 11.17 (brs, 1H), 9.68 (brs, 1H), 8.72 (brs, 1H), 8.15-8.13 (m, 2H), 7.37-7.34 (m, 1H), 7.05-6.99 (m, 2H), 6.91 (brd, J=8.7 Hz, 1H), 3.66-3.64 (m, 2H), 3.55-3.41 (m, 3H), 3.38-3.22 (m, 1H), 3.12-3.09 (m, 2H), 3.00-2.97 (m, 1H), 2.76 (d, J=4.8 Hz, 3H), 2.32-2.18 (m, 2H), 1.99-1.86 (m, 3H), 1.77-1.71 (m, 1H); ESI-MS (m/z, %): 387 (MH+, free base, 100), 194 (19); ESI-HRMS calculated for C20H27N4S2 (MH+, free base): 387.1671, observed: 387.1654; HPLC purity: 97% by area.

Workup

  1. customThe precipitate was collected
  2. washrinsed with ether
  3. dissolutionThe precipitate was dissolved in methanol
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8ab2da29459b4451be7820c5403b847e
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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