Hydrochloric Acid → HCID 136351945, compound

HRID 1271232Notes

Reaction equation

HRID 1271232 reaction equation
CC(C)([O-])C.[Na+].[O:7]=[C:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=2)[NH:9]1.Cl[C:22]1[C:23]2[CH:30]=[CH:29][S:28][C:24]=2[N:25]=[CH:26][N:27]=1.Cl>CN1CCCC1=O.O>[CH3:20][O:19][C:17]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([OH:7])=[C:16]2[C:22]1[C:23]2[CH:30]=[CH:29][S:28][C:24]=2[N:25]=[CH:26][N:27]=1)=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7366184-Chlorothieno[2,3-d]pyrimidineHCID 2773516Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 136351945HCID 136351945, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

Sodium tert-butoxide (40.3 mg, 0.42 mmol) and methyl 2-oxo-5-indolinecarboxylate (17.6 mg, 0.092 mmol) in N-methylpyrrolidinone (1 mL) under nitrogen atmosphere were stirred for 5 min at room temperature. A solution of 4-chlorothieno[2,3-d]pyrimidine (0.1 mL, 0.84 M, corresponding to 14.3 mg, 0.084 mmol) in N-methylpyrrolidinone was added and the reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with water (20 mL) and acidified with hydrochloric acid (1 M) and extracted with ethyl acetate (2×15 mL). The combined organic layer was washed with brine, dried with sodium sulphate, filtered and concentrated. The crude product was triturated with methylene chloride to give 10 mg (36% yield) of the title compound as a bronze solid. MS (AP−) m/z 324 (M−1).

Workup

  1. extractionextracted with ethyl acetate (2×15 mL)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried with sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was triturated with methylene chloride

Sources & evidence

ORD record
ord-ac853ccc715e4bd786b5392338890135
Source dataset
uspto-grants-2007_04
Patent number
US07205314B2

Reaction notes

Loading…