HCID 86713687, compound → HCID 71584810, compound

HRID 1430558Notes

Reaction equation

HRID 1430558 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:31])[N:10]([CH2:29][CH3:30])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([N:18](CC2C=CC(OC)=CC=2)[CH3:19])[CH:12]=3)=[CH:6][C:5]([NH:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[C:38]([CH2:43][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[CH:37]=2)=[O:34])=[C:4]([F:50])[CH:3]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:31])[N:10]([CH2:29][CH3:30])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH3:19])[CH:12]=3)=[CH:6][C:5]([NH:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[C:38]([CH2:43][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[CH:37]=2)=[O:34])=[C:4]([F:50])[CH:3]=1

Participants

3

Reactant 1

HCID 86713687HCID 86713687, compound

Product 1

HCID 71584810HCID 71584810, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1-(4-chloro-5-(1-ethyl-7-((4-methoxybenzyl)(methyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(4-fluoro-3-(morpholinomethyl)phenyl)urea (152 mg, 0.216 mmol) in TFA (3 mL) was stirred under Ar for 3 h. The mixture was concentrated to dryness, treated with EtOAc and satd. NaHCO3 and stirred for 0.5 h. The resulting solid was collected via filtration and dried to afford 1-(4-chloro-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(4-fluoro-3-(morpholinomethyl)phenyl)urea (111 mg, 76% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.12 (s, 1H), 8.63 (d, J=2.5 Hz, 1H), 8.41 (s, 1H), 8.15 (d, J=8.7 Hz, 1H), 7.73 (s, 1H), 7.53 (d, J=11.0 Hz, 1H), 7.47 (dd, J=6.5, 2.8 Hz, 1H), 7.30 (ddd, J=8.9, 4.5, 2.8 Hz, 1H), 7.10-7.01 (m, 2H), 6.24 (s, 1H), 4.14 (q, J=7.1 Hz, 2H), 3.53 (t, J=4.4 Hz, 4H), 3.44 (s, 2H), 2.86 (d, J=4.9 Hz, 3H), 2.35 (m, 4H), 1.20 (t, J=7.0 Hz, 3H); MS (ESI) m/z: 583.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiontreated with EtOAc and satd
  3. stirringNaHCO3 and stirred for 0.5 h
  4. filtrationThe resulting solid was collected via filtration
  5. customdried

Sources & evidence

ORD record
ord-f404329bcaf0476bad1cad4cb386a841
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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