3-Fluorophenyl isocyanate → HCID 86713689, compound

HRID 1257272Notes

Reaction equation

HRID 1257272 reaction equation
[NH2:1][C:2]1[C:3]([F:33])=[CH:4][C:5]([Cl:32])=[C:6]([C:8]2[C:9](=[O:31])[N:10]([CH:28]([CH3:30])[CH3:29])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH:12]=3)[CH:7]=1.[F:34][C:35]1[CH:36]=[C:37]([N:41]=[C:42]=[O:43])[CH:38]=[CH:39][CH:40]=1>C1COCC1>[Cl:32][C:5]1[C:6]([C:8]2[C:9](=[O:31])[N:10]([CH:28]([CH3:29])[CH3:30])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH:12]=3)=[CH:7][C:2]([NH:1][C:42]([NH:41][C:37]2[CH:38]=[CH:39][CH:40]=[C:35]([F:34])[CH:36]=2)=[O:43])=[C:3]([F:33])[CH:4]=1

Participants

4

Reactant 2

HCID 1230643-Fluorophenyl isocyanateHCID 86713690HCID 86713690, compound

Product 1

HCID 86713689HCID 86713689, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(5-amino-2-chloro-4-fluorophenyl)-1-isopropyl-7-((4-methoxybenzyl)amino)-1,6-naphthyridin-2(1H)-one (0.11 g, 0.236 mmol) in THF (5 mL) was treated with TEA (0.1 mL) and 3-fluorophenyl isocyanate (0.032 mL, 0.259 mmol) and stirred at RT for 5 h. The mixture was concentrated to dryness, treated with DCM and the solid collected via filtration and dried to afford 1-(4-chloro-2-fluoro-5-(1-isopropyl-7-((4-methoxybenzyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)phenyl)-3-(3-fluorophenyl)urea (94 mg, 66% yield). MS (ESI) m/z: 604.1 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiontreated with DCM
  3. filtrationthe solid collected via filtration
  4. customdried

Sources & evidence

ORD record
ord-2671cdbcaae348ceb0b4d9402f09577c
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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