Potassium Carbonate → HCID 18320759, compound

HRID 1699529

Reaction equation

HRID 1699529 reaction equation
[C:1]([C:3]1[N:4]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=2[O:37][CH3:38])[C:5](=[O:27])[N:6]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19](C)[CH:18]=2)[C:7]=1[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)#[N:2].[CH3:39][S:40]([O:43][CH2:44][CH2:45][CH2:46]OS(C)(=O)=O)(=[O:42])=[O:41].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:39][S:40]([O:43][CH2:44][CH2:45][CH2:46][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([C:7]2[N:6]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[C:5](=[O:27])[N:4]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=3[O:37][CH3:38])[C:3]=2[C:1]#[N:2])=[CH:9]1)(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 275321,3-Propanediol, 1,3-dimethanesulfonateHCID 18320729HCID 18320729, compound

Product 1

HCID 18320759HCID 18320759, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution 0.15 g (0.298 mmol) of the product from step b) in 2 ml of DMF was 0.40 g (1.72 mmol) of 1,3-propandiol bismethansulfonate and 0.50 g (3.62 mmol) of K2CO3. The mixture was stirred at 70° C. overnight and partitioned between EtOAc and water. The organic phase was washed with water and brine and finally evaporated. The residue was purified by chromatography on silica furnishing 0.11 g (59%) of the sub-title compound.

Workup

  1. custompartitioned between EtOAc and water
  2. washThe organic phase was washed with water and brine
  3. customfinally evaporated
  4. customThe residue was purified by chromatography on silica furnishing 0.11 g (59%) of the sub-title compound

Sources & evidence

ORD record
ord-8490e5a0de73423d845d5d859fab2c15
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Linked notes

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