Hydrochloric Acid → HCID 178511898, compound

HRID 1917243Notes

Reaction equation

HRID 1917243 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[NH:30])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[N:16]([CH:17]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)[CH2:15][CH2:14][S:13][C:12]=2[CH:29]=1.Cl>CO>[NH:19]1[CH2:20][CH2:21][CH:17]([N:16]2[CH2:15][CH2:14][S:13][C:12]3[CH:29]=[C:8]([NH:7][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[NH:30])[CH:9]=[CH:10][C:11]2=3)[CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452061HCID 178452061, compound

Product 1

HCID 178511898HCID 178511898, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 3-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)pyrrolidine-1-carboxylate (0.24 g, 0.554 mmol) in MeOH (5 mL) was treated with 1N HCl solution (9.98 mL, 9.98 mmol) at room temperature. The resulting mixture was refluxed for 30 minutes and brought to room temperature. The mixture was filtered and quenched with 1N NaOH (10 mL). The mixture was diluted with water (50 mL) and extracted with CH2Cl2 (2×50 mL). The organic phase was washed with brine (50 mL) and dried (Na2SO4). The crude material was subject to flash chromatography on silica gel (5-20% 2M NH3MeOH/CH2Cl2). The collected fractions gave compound 30 as yellow foam (0.15 g, 79%). 1H NMR (DMSO-d6) δ 7.69 (d, J=3.0 Hz, 1H), 7.56 (dd, J=0.9, 4.9 Hz, 1H), 7.07 (dd, J=3.9, 4.9 Hz, 1H), 6.79 (d, J=9.0 Hz, 1H), 6.52-6.49 (m, 2H), 6.31 (brs, 2H), 4.26-4.17 (m, 1H), 3.42-3.22 (m, 2H), 3.10-2.90 (m, 4H), 2.83-2.69 (m, 2H), 2.07-1.96 (m, 1H), 1.68-1.57 (m, 1H); ESI-MS (m/z, %): 347, 345 (MH+, 72), 278, 276 (100).

Workup

  1. temperatureThe resulting mixture was refluxed for 30 minutes
  2. custombrought to room temperature
  3. filtrationThe mixture was filtered
  4. customquenched with 1N NaOH (10 mL)
  5. additionThe mixture was diluted with water (50 mL)
  6. extractionextracted with CH2Cl2 (2×50 mL)
  7. washThe organic phase was washed with brine (50 mL)
  8. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-ecfee20bb11a4c3ea7fa35716f57279d
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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