Triethylamine → HCID 136344288, compound

HRID 455149Notes

Reaction equation

HRID 455149 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][C:19](=[N:21][OH:22])[NH2:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C(N(CC)CC)C.[C:30](Cl)(=O)[O:31]C1C=CC=CC=1>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][C:19]3[NH:20][C:30](=[O:31])[O:22][N:21]=3)=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 86700660HCID 86700660, compound

Product 1

HCID 136344288HCID 136344288, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(6-fluoro-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-3-yl)-N′-hydroxyacetimidamide (0.040 g, 0.13 mmol) and triethylamine (0.025 mL, 0.198 mmol) in CHCl3 (1 mL) was treated with phenyl carbonochloridate (0.018 mL, 0.19 mmol) and stirred for 1 h. The reaction mixture was washed with water (30 mL) and dichloromethane (30 mL). The organic solution was dried with Na2SO4, evaporated under vacuum. The crude product was purified by HPLC to provide the title product. M/e+ 329 for C16H11F2N4O2 (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.69 (dd, J=4.0, 2.2 Hz, 1H), 7.77 (dd, J=9.9, 4.7 Hz, 1H), 7.69 (m, 2H), 7.62 (m, 2H), 7.29 (m, 2H), 4.45 (s, 2H) ppm.

Workup

  1. washThe reaction mixture was washed with water (30 mL) and dichloromethane (30 mL)
  2. dry with materialThe organic solution was dried with Na2SO4
  3. customevaporated under vacuum
  4. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-ddcd3ca5e3cc4dbc9917e36cecd68efb
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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