Hydrochloric Acid → HCID 178484220, compound

HRID 424496Notes

Reaction equation

HRID 424496 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[CH:19][C:20]([NH:22][C:23]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)=[NH:24])=[CH:21][C:13]1=2)C(=O)OC(C)(C)C.[ClH:30]>CO>[ClH:30].[ClH:30].[CH3:1][NH:2][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[CH:19][C:20]([NH:22][C:23]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)=[NH:24])=[CH:21][C:13]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178484221tert-butyl methyl(2-(6-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethyl)carbamate

Product 1

HCID 178484220HCID 178484220, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl methyl(2-(6-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethyl)carbamate (0.07 g, 0.168 mmol) in HPLC grade MeOH (10 mL) was added 3M hydrochloric acid (0.56 mL, 1.681 mmol). The resulting yellow solution was heated to reflux under an atmosphere of argon. After 60 minutes, the reaction was cooled to room temperature and concentrated. The residue was diluted with H2O (20 mL) and rinsed sequentially with CH2Cl2 (20 mL) and EtOAc (20 mL). The aqueous layer was concentrated and dried to yield the title compound 10 as a yellow solid (37 mg, 56.5%). 1H NMR (DMSO-d6) δ 11.37 (brs, 1H), 9.72 (brs, 1H), 9.23 (brs, 2H), 8.66 (brs, 1H), 8.21-8.08 (m, 2H), 7.37 (app t, 1H, J=4.4 Hz), 7.03 (s, 1H), 6.84 (d, 1H, J=8.3 Hz), 6.60 (d, 1H, J=7.3 Hz), 4.31-4.20 (m, 2H), 3.70-3.45 (m, 2H, merged with H2O peak), 3.40-3.34 (m, 2H), 3.18-3.02 (m, 2H), 2.60-2.50 (m, 3H); ESI-MS (m/z, %): 317 (MH+, free base, 100); ESI-HRMS calculated for C16H21N4OS (MH+, free base): 317.1430; observed: 317.1422.

Workup

  1. temperatureThe resulting yellow solution was heated
  2. temperatureto reflux under an atmosphere of argon
  3. concentrationconcentrated
  4. additionThe residue was diluted with H2O (20 mL)
  5. washrinsed sequentially with CH2Cl2 (20 mL) and EtOAc (20 mL)
  6. concentrationThe aqueous layer was concentrated
  7. customdried

Sources & evidence

ORD record
ord-c6ee00bbae0042b18965be8802cba511
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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