Hydrochloric Acid → HCID 178464394, compound

HRID 424600Notes

Reaction equation

HRID 424600 reaction equation
[CH2:1]([N:3]([CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][S:16][C:15]2[CH:19]=[C:20]([NH:23][C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[NH:25])[CH:21]=[CH:22][C:14]1=2)C(=O)OC(C)(C)C)[CH3:2].Cl.[OH-].[Na+]>CO.O>[CH2:1]([NH:3][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][S:16][C:15]2[CH:19]=[C:20]([NH:23][C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[NH:25])[CH:21]=[CH:22][C:14]1=2)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178464396HCID 178464396, compound

Product 1

HCID 178464394HCID 178464394, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl ethyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (0.4 g, 0.896 mmol) in methanol (10 mL) was treated with 3 N HCl (3.88 mL, 11.64 mmol) and stirred at reflux for 1.5 hours. The mixture was cooled to room temperature, diluted with water (20 mL), and basified with 1N NaOH. The product was extracted into dichloromethane (2×25 mL). The combined organic layer was dried (Na2SO4) and concentrated. The crude material was subjected to column chromatography on silica gel (5:95 (2M NH3 in MeOH):CH2Cl2) to give a yellow solid (0.142 g, 45.8%). 1H-NMR (DMSO-d6) δ 7.69 (dd, J=0.9, 3.6 Hz, 1H), 7.56 (d, J=5.1 Hz, 1H), 7.07 (dd, J=3.6, 4.8 Hz, 1H), 6.72 (d, J=8.7 Hz, 1H), 6.49 (dd, J=2.1, 8.4 Hz, 1H), 6.45 (d, J=2.1 Hz, 1H), 6.31 (brs, 2H), 3.55-3.51 (m, 2H), 3.30-3.24 (m, 2H), 3.04-3.00 (m, 2H), 2.62 (t, J=6.9 Hz, 2H), 2.56 (q, J=7.2 Hz, 2H), 1.01 (t, J=7.2 Hz, 3H); ESI-MS (m/z, %): 347 (MH+, 75%), 276 (100%); HPLC purity: 99.5% by area.

Workup

  1. temperatureat reflux for 1.5 hours
  2. extractionThe product was extracted into dichloromethane (2×25 mL)
  3. dry with materialThe combined organic layer was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-abca9bdd41f34f21984a54622d196831
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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