Trifluoroacetic acid → HCID 178484226, compound

HRID 424537Notes

Reaction equation

HRID 424537 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[NH:29])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[N:16]([CH2:17][CH2:18][N:19](C)[C:20](=O)OC(C)(C)C)[CH2:15][CH2:14][S:13][C:12]=2[CH:28]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:20][NH:19][CH2:18][CH2:17][N:16]1[CH2:15][CH2:14][S:13][C:12]2[CH:28]=[C:8]([NH:7][C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[NH:29])[CH:9]=[CH:10][C:11]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178484228HCID 178484228, compound

Product 1

HCID 178484226HCID 178484226, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 2-(7-(furan-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamate (0.823 g, 1.978 mmol) in CH2Cl2 (20 mL) was cooled to 0° C. and was treated with trifluoroacetic acid (5 mL). The mixture was stirred at 0° C. under argon atmosphere for 2 hours. The mixture was quenched with 1N NaOH solution (70 mL) and transferred to a separatory funnel. The solution 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 concentrated and subjected to flash chromatography on silica gel (5-15% (2M NH3 MeOH):CH2Cl2). The collected fractions were concentrated to give compound 20 as a yellow viscous oil (0.47 g, 76%). 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.44-7.43 (m, 1H), 6.77-6.74 (m, 2H), 6.70 (d, J=2.4 Hz, 1H), 6.62 (dd, J=2.4, 8.7 Hz, 1H), 3.59-3.56 (m, 2H), 3.47 (s, 1H), 3.40 (t, J=6.6 Hz, 2H), 3.05-3.01 (m, 2H), 2.81 (t, J=6.3, 2H), 2.48 (s, 3H); ESI-MS (m/z, %): 319, 317 (MH+, 96), 260 (100).

Workup

  1. customThe mixture was quenched with 1N NaOH solution (70 mL)
  2. customtransferred to a separatory funnel
  3. additionThe solution was diluted with water (50 mL)
  4. extractionextracted with CH2Cl2 (2×50 mL)
  5. washThe organic phase was washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationThe crude material was concentrated
  8. concentrationThe collected fractions were concentrated

Sources & evidence

ORD record
ord-d727556847ce417cb5fe7954b47012c4
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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