Anisole → HCID 86713691, compound

HRID 1430563Notes

Reaction equation

HRID 1430563 reaction equation
[Cl:1][C:2]1[C:7]([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]CC2C=CC(OC)=CC=2)[CH:12]=3)=[CH:6][C:5]([NH:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=2)=[O:34])=[C:4]([F:43])[CH:3]=1.C1(OC)C=CC=CC=1>C(O)(C(F)(F)F)=O>[NH2:18][C:13]1[CH:12]=[C:11]2[C:16]([CH:17]=[C:8]([C:7]3[C:2]([Cl:1])=[CH:3][C:4]([F:43])=[C:5]([NH:32][C:33]([NH:35][C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=4)=[O:34])[CH:6]=3)[C:9](=[O:31])[N:10]2[CH:28]([CH3:30])[CH3:29])=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 86713689HCID 86713689, compound

Product 1

HCID 86713691HCID 86713691, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 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 (0.094 g, 0.156 mmol) and anisole (0.085 mL, 0.778 mmol) was stirred in TFA (1 mL) at RT for 3 h. The mixture was concentrated to dryness, treated with EtOAc and satd. NaHCO3 and stirred for 1 h. The resulting solid was collected via filtration and dried to afford 1-(5-(7-amino-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-chloro-2-fluorophenyl)-3-(3-fluorophenyl)urea (70 mg, 93% yield). MS (ESI) m/z: 484.1 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiontreated with EtOAc and satd
  3. filtrationThe resulting solid was collected via filtration
  4. customdried

Sources & evidence

ORD record
ord-272fc9f834434edda5bb10800e4d5cc3
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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