Dimethylformamide → HCID 59593173, compound

HRID 2262189Notes

Reaction equation

HRID 2262189 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.[CH3:19][C:20]([NH:22][C:23]1[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][CH:24]=1)=[O:21].C([O-])([O-])=O.[K+].[K+].C[N:37]([CH:39]=O)C>>[NH:37]1[C:39]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:29][C:27]5[CH:28]=[C:23]([NH:22][C:20](=[O:21])[CH3:19])[CH:24]=[CH:25][CH:26]=5)=[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 6228DimethylformamideHCID 7604m-AminoacetanilideHCID 11430Potassium CarbonateHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 59593173HCID 59593173, 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-aminoacetanilide (39 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 301 after reverse phase HPLC purification (39 mg). MS (Q1) 500 (M)+

Workup

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

Sources & evidence

ORD record
ord-f31878db97f14b4091ce2f8dcb0b4335
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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