Triethylamine → HCID 5329096, compound

HRID 394766Notes

Reaction equation

HRID 394766 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[CH:18]=[C:17]([S:19]([CH2:22][CH2:23]O)(=[O:21])=[O:20])[N:16]=[CH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[CH:18]=[C:17]([S:19]([CH:22]=[CH2:23])(=[O:21])=[O:20])[N:16]=[CH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 5329095HCID 5329095, compound

Product 1

HCID 5329096HCID 5329096, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a 0-5° C. stirred suspension of 2-[4-(3-bromo-phenylamino)-pyrido[3,4-d]pyrimidine-6-sulfonyl]-ethanol (41 mg, 0.1 mmol), and triethylamine (31 μL, 0.22 mmol) in dichloromethane (0.5 mL) under N2 was added dropwise methanesulfonyl chloride (9.3 μL, 0.12 mmol). Additional charges of methanesulfonyl chloride (9.3 μL, 9.3 μL) were added after 45 minutes, and 1.5 hours, the latter with additional triethylamine (50 μL). After reaction for a total of 2.5 hours, the cold solution was quenched with 5% aqueous sodium bicarbonate, then extracted with ethyl acetate (2×). The combined organic extracts were dried (MgSO4) then filtered through a pad of flash SiO2. The filtrate was concentrated to a solid that was crystallized from ethyl acetate to leave the product (17 mg, 44%), Mp 214-217° C.

Workup

  1. custom1.5 hours
  2. customAfter reaction for a total of 2.5 hours
  3. customthe cold solution was quenched with 5% aqueous sodium bicarbonate
  4. extractionextracted with ethyl acetate (2×)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationthen filtered through a pad of flash SiO2
  7. concentrationThe filtrate was concentrated to a solid
  8. customthat was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-eea3867d17484e43bb34256e68dd9ebf
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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