Trifluoroacetic acid → HCID 58838514, compound

HRID 2374463Notes

Reaction equation

HRID 2374463 reaction equation
[O:1]([C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:16][C:17]1[N:22]=[C:21]([NH:23]C(=O)OC(C)(C)C)[CH:20]=[CH:19][CH:18]=1.FC(F)(F)C(O)=O>N1C=CC=CC=1>[NH2:23][C:21]1[N:22]=[C:17]([NH:16][S:12]([C:9]2[CH:10]=[CH:11][C:6]([O:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:7][CH:8]=2)(=[O:14])=[O:13])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5179904-Butoxybenzenesulfonyl ChlorideHCID 45092083tert-Butyl (6-aminopyridin-2-yl)carbamate

Product 1

HCID 58838514HCID 58838514, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The 4-butoxylphenyl sulfonyl chloride (160 μmol, 2.0 eq, 400 μL of a 0.40 M in anhydrous pyridine) and tert-butyl (6-aminopyridin-2-yl)carbamate (80 μmol, 1.0 eq, 400 μL of a 0.20 M in anhydrous pyridine) was added into a test tube (75×10 mm, dried by heating at 110° C. for 16 h before use) equipped with a stir bar. The test tube was covered with Parafilm, and was stirred for 24 h at ambient temperature. The solvent (pyridine) was evaporated in vacuo. Trifluoroacetic acid (320 μL, 52.0 eq., excess, neat) was added into the test tube. The test tube was capped and vortexed for 5 h at ambient temperature. The excess TFA was removed in vacuo, and the residue was dissolved in DMSO (1.340 mL) and purified by HPLC. 1H NMR (500 MHz, DMSO-d6) δ: 7.73 (d, J=7.7 Hz, 2H), 7.21 (t, J=7.2 Hz, 1H), 6.96 (d, J=6.9 Hz, 1H), 6.10 (d, J=6.1 Hz, 1H), 5.92 (d, J=5.9 Hz, 1H), 3.96 (t, J=6.6 Hz, 1H)), 1.64 (m, 2H), 1.37 (m, 2H), 0.87 (t, J=7.4 Hz, 3H). LRMS m/z: 322.0.

Workup

  1. custom(75×10 mm, dried by heating at 110° C. for 16 h before use)
  2. customequipped with a stir bar
  3. customThe solvent (pyridine) was evaporated in vacuo
  4. customThe test tube was capped
  5. waitvortexed for 5 h at ambient temperature
  6. customThe excess TFA was removed in vacuo
  7. dissolutionthe residue was dissolved in DMSO (1.340 mL)
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-76f1f02bd1fe401aaa7c8d5a02f10a95
Source dataset
uspto-grants-2008_12
Patent number
US07462634B2

Reaction notes

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