Water → HCID 89524919, compound

HRID 1466029Notes

Reaction equation

HRID 1466029 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][N:12]([C:23](=[O:26])[CH2:24]Cl)[CH2:13][CH2:14][NH:15]C(=O)OC(C)(C)C)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+].O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][NH:15][CH2:24][C:23]2=[O:26])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 131732673HCID 131732673, compound

Product 1

HCID 89524919HCID 89524919, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-Butyl (2-{[2-(3-bromo-4-cyanophenyl)ethyl](chloroacetyl)amino}ethyl)carbamate (530 mg, 1.2 mmol) in 5 mL of DCM was added 2 mL of TFA and the mixture was stirred at RT for 3 hours, then concentrated in vacuo. The residue was redissolved in ethanol (2 mL) and added K2CO3 (169 mg, 1.22 mmol). The mixture was stirred at reflux for 1.5 hours. Then water (10 ml) was added, and the mixture was extracted with ethyl acetate (5 mL×3), dried over Na2SO4 and concentrated in vacuo to give the title product. 1H-NMR (400 MHz, CD3CN) δ 7.68-7.70 (m, 2H), 7.39 (dd, J=1.6, 7.6 Hz, 1H), 3.55 (t, J=5.6 Hz, 2H), 3.27 (s, 2H), 3.18 (t, J=5.6 Hz, 2H), 2.88-2.92 (m, 4H). MS m/z: 308 [M+1]+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was redissolved in ethanol (2 mL)
  3. stirringThe mixture was stirred
  4. temperatureat reflux for 1.5 hours
  5. extractionthe mixture was extracted with ethyl acetate (5 mL×3)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa6cda3f36e647cbaaec06fa73c70174
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…