N-(3-Aminopropyl)morpholine → 1-(4-{4-Cyano-3-[(3-morpholin-4-ylpropyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea

HRID 871032Notes

Reaction equation

HRID 871032 reaction equation
Cl[C:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=3[F:26])=[O:17])=[CH:11][CH:10]=2)[S:4][N:3]=1.[O:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][NH2:36])[CH2:29][CH2:28]1.C([O-])([O-])=O.[Na+].[Na+].[Cl-].[Na+].O>CCOC(C)=O>[C:7]([C:6]1[C:2]([NH:36][CH2:35][CH2:34][CH2:33][N:30]2[CH2:31][CH2:32][O:27][CH2:28][CH2:29]2)=[N:3][S:4][C:5]=1[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[F:26])=[O:17])=[CH:11][CH:10]=1)#[N:8]

Participants

5

Reactant 3

HCID 61055N-(3-Aminopropyl)morpholineHCID 866892241-[4-(3-Chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)ureaHCID 131732541Na2CO3 brine

Product 1

HCID 866892371-(4-{4-Cyano-3-[(3-morpholin-4-ylpropyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)ureaYield 16%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-[4-(3-chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea (50 mg, 0.13 mmol) and 0.2 mL 3-morpholinopropylamine was heated at 70° C. for 18 hours. Then an aqueous Na2CO3/brine mixture and EtOAc workup was done, and the resulting material chromatographed eluting with CHCl3/MeOH. The resulting solid was then triturated with a 1:1/CHCl3/hexane mixture which gave the title compound as a pale yellow solid (10 mg, 16%).

Workup

  1. customthe resulting material chromatographed
  2. washeluting with CHCl3/MeOH
  3. customThe resulting solid was then triturated with a 1:1/CHCl3/hexane mixture which

Sources & evidence

ORD record
ord-c88df2a1e72848e1bf62c61691c3d5c3
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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