3-Aminobenzamide → HCID 59593178, compound

HRID 2098766Notes

Reaction equation

HRID 2098766 reaction equation
Br[CH2:2][C:3]1[S:11][C:10]2[C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7](Cl)=[N:6][C:5]=2[CH:4]=1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([NH2:25])=[O:24].C([O-])([O-])=O.[K+].[K+].C[N:36]([CH:38]=O)C>>[NH:36]1[C:38]2[C:10](=[C:5]([C:7]3[N:8]=[C:9]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)[C:10]4[S:11][C:3]([CH2:2][NH:19][C:20]5[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=5)[C:23]([NH2:25])=[O:24])=[CH:4][C:5]=4[N:6]=3)[CH:4]=[CH:3][CH:2]=2)[CH:9]=[N:8]1

Participants

5

Reactant 4

HCID 16453-AminobenzamideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 59593178HCID 59593178, compound

Procedure

To a solution of 6-(bromomethyl)-2-chloro-4-morpholinothieno[3,2-d]pyrimidine 30 from Example 9 (90 mg, 0.3 mmol) in DMF (3 mL) was added 3-aminobenzamide (35 mg, 0.3 mmol) and K2CO3 (50 mg, 0.4 mmol). The resulting solution stirred at room temperature overnight then was concentrated in vacuo. The residue was diluted with water and filtered. The crude product was utilized in a Suzuki coupling using General Procedure A with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 to provide 303 after reverse phase HPLC purification (28 mg). MS (Q1) 486 (M)+

Workup

  1. concentrationthen was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-df17770018fe49ae96ea64fae93b9aca
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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