Water → HCID 71585133, compound

HRID 1430522Notes

Reaction equation

HRID 1430522 reaction equation
[C:1]([N:4]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:21]3[CH:26]=[C:25]([NH:27][C:28]([NH:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:29])[C:24]([F:37])=[CH:23][C:22]=3[F:38])[C:14](=[O:20])[N:15]2[CH2:18][CH3:19])=[CH:10][N:9]=1)C(=O)C)(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].O>CO>[C:1]([NH:4][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:21]3[C:22]([F:38])=[CH:23][C:24]([F:37])=[C:25]([NH:27][C:28]([NH:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[O:29])[CH:26]=3)[C:14](=[O:20])[N:15]2[CH2:18][CH3:19])=[CH:10][N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86713664HCID 86713664, compound

Product 1

HCID 71585133HCID 71585133, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-acetyl-N-{3-[2,4-difluoro-5-(3-phenyl-ureido)-phenyl]-1-ethyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-7-yl}-acetamide (100 mg, 0.19 mmol) in MeOH (2 mL) was added K2CO3 (79 mg, 0.57 mmol) and water (1 mL), and the mixture was stirred overnight at RT. MeOH was removed under reduced pressure and the residue was diluted with water (8 mL). The mixture was extracted with EtOAc to give a crude product which purified by prep-HPLC to give 1-(5-(7-acetamido-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)-3-phenylurea (32 mg, 23% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.85 (s, 1H), 9.08 (s, 1H), 8.74 (s, 1H), 8.61 (s, 1H), 8.27 (s, 1H), 8.21-8.16 (m, 1H), 8.07 (s, 1H), 7.45-7.40 (m, 3H), 7.30-7.26 (m, 2H), 7.00-6.96 (m, 1H), 4.24-4.18 (q, J=6.8 Hz, 2H), 2.16 (s, 3H), 1.28-1.25 (t, J=6.8 Hz, 3H); MS (ESI) m/z: 478.3 [M+H]+.

Workup

  1. customMeOH was removed under reduced pressure
  2. additionthe residue was diluted with water (8 mL)
  3. extractionThe mixture was extracted with EtOAc
  4. customto give a crude product which
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-0a0829de2337487189bd855159e9fd52
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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