Hydrogen Bromide → HCID 24780958, compound

HRID 2241824Notes

Reaction equation

HRID 2241824 reaction equation
[F:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[CH:19]=[C:18]([O:20]C)[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][N:6]=1.Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>[F:1][CH2:2][CH2:3][NH:4][C:5]1[N:6]=[CH:7][C:8]([C:11]2[O:12][C:13]3[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 24780800HCID 24780800, compound

Product 1

HCID 24780958HCID 24780958, compoundYield 21.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

To N-(2-fluoroethyl)-5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-amine (0.18 mmol), in a microwave vial with a stir bar, was added tetrabutylammonium bromide (0.02 mmol) and hydrobromic acid 48%, w/w aq soln (5.0 mL). The reaction vessel was sealed and heated at 120° C. for 10 min. LCMS showed remaining starting material and the reaction was run an additional 10 min. The reaction mixture was neutralized with sat NaHCO3 (100 mL), extracted with (3×50 mL) CH2Cl2, the combined organic layers were dried (Na2SO4) and evaporated to give 33.1 mg as a brown oil. Purified on prep HPLC to give 10.4 mg of the title compound as a tan solid after lyophilization. 1H NMR (400 MHz, Chloroform-d/MeOH-d4 1:1) δ ppm 8.75 (d, 1H) 8.05 (dd, 1H) 7.42 (d, 1H) 7.00 (d, 1H) 6.82 (dd, 1H) 6.63 (d, 1H) 4.62-4.66 (m, 1H) 4.50-4.54 (m, 1H) 3.71-3.76 (m, 1H) 3.64-3.69 (m, 1H); 19F (1H decoupled) NMR (400 MHz, Chloroform-d/MeOH-d4) δ ppm −224.8; MS m/z 274 (M+H).

Workup

  1. customThe reaction vessel was sealed
  2. extractionextracted with (3×50 mL) CH2Cl2
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. customevaporated
  5. customto give 33.1 mg as a brown oil
  6. customPurified on prep HPLC

Sources & evidence

ORD record
ord-a08188cf4619461299284932e5e8e25c
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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