3-Fluorophenyl isocyanate → HCID 89443462, compound

HRID 1771129Notes

Reaction equation

HRID 1771129 reaction equation
[NH2:1][C:2]1[C:3]([F:21])=[C:4]([C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[N:14]3)=[O:10])[C:5]([F:8])=[CH:6][CH:7]=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]=[C:30]=[O:31])[CH:24]=1>C(Cl)Cl>[F:21][C:3]1[C:4]([C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[N:14]3)=[O:10])=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[NH:1][C:30]([NH:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=1)=[O:31]

Participants

4

Reactant 2

HCID 1230643-Fluorophenyl isocyanateHCID 89462331HCID 89462331, compound

Product 1

HCID 89443462HCID 89443462, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-2,6-difluorophenyl)(quinoxalin-6-yl)methanone (40 mg, 0.15 mmol, 1.0 eq.) in DCM (5 mL) were added TEA (42.4 mg, 0.42 mmol, 3.0 eq.) and 1-fluoro-3-isocyanatobenzene (23.3 mg, 0.17 mmol, 1.2 eq.). The resulting mixture was stirred at rt for 1 h, then concentrated. The resulting residue was purified via flash column chromatography (PE/EA=1/1, v/v) to afford 1-(2,4-difluoro-3-(quinoxaline-6-carbonyl)phenyl)-3-(3-fluorophenyl)urea (10.5 mg, 16.7%). LRMS (M−H+) m/z caculated 423.1. found 423.1. 1H NMR (DMSO-d6, 400 MHz) δ 9.31 (s, 1H), 9.11-9.13 (d, 2H), 8.76 (s, 1H), 8.46 (s, 1H), 8.33-8.34 (m, 3H), 7.49-7.52 (d, 1H), 7.32-7.35 (m, 2H), 7.10-7.12 (d, 1H), 6.82 (t, 1H).

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was purified via flash column chromatography (PE/EA=1/1

Sources & evidence

ORD record
ord-e90eca4e9429412eba9febc6ab645165
Source dataset
uspto-grants-2016_02
Patent number
US09249110B2

Reaction notes

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