Sodium Bicarbonate → HCID 11180559, compound

HRID 1837353Notes

Reaction equation

HRID 1837353 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH3:11])=[CH:5][C:4]=1[NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19](F)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:26]#[N:27].C(=O)(O)[O-].[Na+].[O:33]=[S:34]1(=[O:44])[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][OH:43])[CH2:36][CH2:35]1>>[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH3:11])=[CH:5][C:4]=1[NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:43][CH2:42][CH2:41][CH2:40][N:37]3[CH2:36][CH2:35][S:34](=[O:44])(=[O:33])[CH2:39][CH2:38]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:26]#[N:27]

Participants

5

Reactant 4

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 114354734-(3-Hydroxypropyl)thiomorpholine 1,1-DioxideHCID 114861534-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile

Product 1

HCID 11180559HCID 11180559, compound

Conditions

Temperature
100 °C

Procedure

A mixture of sodium (48 mg, 2.1 mmol) in 2 mL of 3-(1,1-dioxothiomorpholinyl)-1-propanol (WO 20047212) is heated at 100° C. for 1 hour. 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile (200 mg, 0.51 mmol) is added and the reaction mixture is heated at 100° C. for 4 hours, then cooled to room temperature. The reaction mixture is poured into saturated sodium bicarbonate and the solids are collected by filtration. The residue is purified by flash column chromatography eluting with 5% methanol in dichloromethane to provide 88 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-[3-(1,1-dioxido-4-thiomorpholinyl)propoxy]-6-methoxy-3-quinolinecarbonitrile, mp 118-120° C.

Workup

  1. temperaturethe reaction mixture is heated at 100° C. for 4 hours
  2. temperaturecooled to room temperature
  3. filtrationthe solids are collected by filtration
  4. customThe residue is purified by flash column chromatography
  5. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-6d561160e12244ba80148b30b4006f1c
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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