2,6-Lutidine → N-{3-[1-(2-fluoro-4-iodophenyl)-3,6,8-trimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-ylamino]phenyl}methanesulfonamide

HRID 75669

Reaction equation

HRID 75669 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2[N:15]([CH3:29])[C:16](=[O:28])[C:17]([CH3:27])=[C:18](OS(C(F)(F)F)(=O)=O)[C:13]=2[C:12](=[O:30])[N:11]([CH3:31])[C:10]1=[O:32].[NH2:33][C:34]1[CH:35]=[C:36]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[CH:37]=[CH:38][CH:39]=1.CN(C)C(=O)C.N1C(C)=CC=CC=1C>CO.O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2[N:15]([CH3:29])[C:16](=[O:28])[C:17]([CH3:27])=[C:18]([NH:33][C:34]3[CH:35]=[C:36]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[CH:37]=[CH:38][CH:39]=3)[C:13]=2[C:12](=[O:30])[N:11]([CH3:31])[C:10]1=[O:32]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 31374DimethylacetamideHCID 2734262N-(3-Aminophenyl)methanesulfamideHCID 59717446Trifluoromethanesulfonic acid 1-(2-fluoro-4-iodophenyl)-3,6,8-trimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester

Product 1

HCID 59717220N-{3-[1-(2-fluoro-4-iodophenyl)-3,6,8-trimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-ylamino]phenyl}methanesulfonamideYield 98.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
130 °C

Procedure

To trifluoromethanesulfonic acid 1-(2-fluoro-4-iodophenyl)-3,6,8-trimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 70 (3.00 g) obtained in Step 6 and N-(3-aminophenyl)methanesulfonamide 44 (1.14 g) were added N,N-dimethylacetamide (6.00 ml) and 2,6-lutidine (0.712 ml), and the mixture was stirred at 130° C. for 4 hrs. After allowing to cool to room temperature, methanol/water [1:2 (volume ratio), 18.0 ml] was added under stirring. The crystals were collected by filtration and dried to give N-{3-[1-(2-fluoro-4-iodophenyl)-3,6,8-trimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-ylamino]phenyl}methanesulfonamide 71 (3.13 g, yield 98%) as a pale-gray solid.

Workup

  1. temperatureto cool to room temperature
  2. stirringunder stirring
  3. filtrationThe crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-da8b3023cc66426ca1651be16752627e
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Linked notes

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