Water → HCID 86713646, compound

HRID 1430496Notes

Reaction equation

HRID 1430496 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:18]1[C:19](=[O:32])[N:20]([CH2:30][CH3:31])[C:21]2[C:26]([CH:27]=1)=[CH:25][N:24]=[C:23]([NH:28][CH3:29])[CH:22]=2.CC#N.[CH3:36][S:37]([OH:40])(=[O:39])=[O:38].O>CCOC(C)=O>[CH3:36][S:37]([OH:40])(=[O:39])=[O:38].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:4][C:3]=1[C:18]1[C:19](=[O:32])[N:20]([CH2:30][CH3:31])[C:21]2[C:26]([CH:27]=1)=[CH:25][N:24]=[C:23]([NH:28][CH3:29])[CH:22]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 6395Methanesulfonic AcidHCID 71584956HCID 71584956, compound

Product 1

HCID 86713646HCID 86713646, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1-(4-chloro-3-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)phenyl)-3-phenylurea (0.166 g, 0.371 mmol) in refluxing MeCN (5 mL) was treated with methanesulfonic acid (0.026 mL, 0.408 mmol), cooled to RT, treated with water, frozen and lyophilized. The resulting material was treated with EtOAc, sonicated and collected via filtration to afford 1-(4-chloro-3-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)phenyl)-3-phenylurea methanesulfonate (172 mg, 85% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.96 (s, 1H), 8.81 (s, 1H), 8.54 (s, 1H), 8.08 (br s, 1H), 7.89 (s, 1H), 7.62 (t, J=1.4 Hz, 1H), 7.45-7.39 (m, 4H), 7.25 (t, J=7.8 Hz, 2H), 6.95 (t, J=7.3 Hz, 1H), 6.57 (s, 1H), 4.18 (q, J=7.1 Hz, 2H), 2.97 (s, 3H), 2.33 (s, 3H), 1.22 (t, J=7.0 Hz, 3H); MS (ESI) m/z: 448.1 [M+H]+.

Workup

  1. temperaturefrozen
  2. customsonicated
  3. filtrationcollected via filtration

Sources & evidence

ORD record
ord-af06b7ae11a6440986f023333d37d128
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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