HCID 178483720, compound → HCID 178483718, compound

HRID 424550Notes

Reaction equation

HRID 424550 reaction equation
[CH3:1][N:2]([CH2:10][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>Cl>[CH3:1][NH:2][CH2:10][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

Participants

3

Reactant 1

HCID 178483720HCID 178483720, compound

Product 1

HCID 178483718HCID 178483718, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of tert-butyl methyl(3-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)propyl)carbamate (0.55 g, 1.231 mmol) in 3M hydrochloric acid (25 mL) was refluxed for 1 hour. The reaction was brought to room temperature, filtered, and washed with water (2×10 mL). The combined aqueous layers were evaporated. The crude material was basified with 3 M NaOH solution (50 mL), and the product was extracted into CH2Cl2 (3×20 mL). The combined CH2Cl2 layers were washed with brine (15 mL) and dried (Na2SO4). The organic solvent was evaporated, and the crude material was purified by column chromatography (5:95 to 1:9 (2M NH3 in MeOH):CH2Cl2) on silica gel to obtain compound 23 (0.4 g, 94%) as a solid. 1H NMR (DMSO-d6) δ 7.68 (dd, 1H, J=1.2, 3.7 Hz), 7.56 (dd, 1H, J=0.9, 5.1 Hz), 7.06 (dd, 1H, J=3.6, 4.9 Hz), 6.70 (d, 1H, J=8.7 Hz), 6.51-6.44 (m, 2H), 6.31 (s, 2H), 3.50-3.47 (m, 2H), 3.32-3.25 (m, 4H), 3.04-3.01 (m, 2H), 2.27 (s, 3H), 1.70-1.61 (m, 2H); ESI-MS (m/z, %): 347 (MH+, 80), 276 (100); HPLC purity: 96.05% by area.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customwas brought to room temperature
  3. filtrationfiltered
  4. washwashed with water (2×10 mL)
  5. customThe combined aqueous layers were evaporated
  6. extractionthe product was extracted into CH2Cl2 (3×20 mL)
  7. washThe combined CH2Cl2 layers were washed with brine (15 mL)
  8. dry with materialdried (Na2SO4)
  9. customThe organic solvent was evaporated
  10. customthe crude material was purified by column chromatography (5:95 to 1:9 (2M NH3 in MeOH):CH2Cl2) on silica gel

Sources & evidence

ORD record
ord-15cd05efc16841b7b64920ea2e6bcc4b
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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