Potassium Carbonate → HCID 86592546, compound

HRID 1432984Notes

Reaction equation

HRID 1432984 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH:17]([CH3:19])[NH:16][C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]1[S:34][C:33]2[CH:35]=[C:36]([Cl:39])[CH:37]=[CH:38][C:32]=2[CH:31]=1>CN(C=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH:17]([CH3:19])[N:16]([CH2:29][C:30]4[S:34][C:33]5[CH:35]=[C:36]([Cl:39])[CH:37]=[CH:38][C:32]=5[CH:31]=4)[C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22394336HCID 22394336, compoundHCID 57054033(3S,5RS)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one

Product 1

HCID 86592546HCID 86592546, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3 S,5RS)-1-(4-Amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one (260 mg, 0.56 mmol), EXAMPLE 88, is dissolved in 5 mL of DMF. Potassium carbonate (193.4 mg, 1.4 mmol) is added followed by the addition of 2-bromomethyl-6-chloro-benzo[b]thiophene (218 mg, 0.84 mmol), EXAMPLE 5. Reaction is left to stir overnight. The crude mixture is purified by reverse phase HPLC (10-70% ACN/H2O) to afford the product (27 mg, 6%) as a clear wax with a melting point of 130-131° C. C24H24ClN5OS MS m/z: 466, 468.

Workup

  1. customReaction
  2. waitis left
  3. customThe crude mixture is purified by reverse phase HPLC (10-70% ACN/H2O)

Sources & evidence

ORD record
ord-591acbb0b0d04a0c9a49578744de4802
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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