Pyridine → (3-Ethynylphenyl)-(6-methanesulfonylaminoquinazoline-4-yl)amine

HRID 1288861Notes

Reaction equation

HRID 1288861 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[CH:20])[CH:14]=1.N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCCl>[C:19]([C:15]1[CH:14]=[C:13]([NH:12][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][S:28]([CH3:27])(=[O:30])=[O:29])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:18]=[CH:17][CH:16]=1)#[CH:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 11492625N4-(3-Ethynylphenyl)quinazoline-4,6-diamine

Product 1

HCID 16045517(3-Ethynylphenyl)-(6-methanesulfonylaminoquinazoline-4-yl)amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title product of Example 8 (100 mg, 0.384 mmol), pyridine (140 μL, 1.68 mmol) and methanesulfonyl chloride (99 μL, 1.26 mmol) were refluxed in 10 mL of 1,2-dichloroethane for 7 hours. The reaction mixture was cooled and evaporated in a vacuo to a residue which was triturated in 10 mL of 1N HCl, filtered and dried in vacuo to yield (3-ethynylphenyl)-(6-methanesulfonylaminoquinazoline-4-yl)amine; 102 mg (78%) mp 248° C. dec.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated in a vacuo to a residue which
  3. customwas triturated in 10 mL of 1N HCl
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-24a0fd6f57644529b03e2766c1523696
Source dataset
uspto-grants-1998_05
Patent number
US05747498

Reaction notes

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