Dichloromethane → 5-chloro-8-fluoro,2-methyl-3-[(4-methylphenyl)sulfonyl]pyrrolo[2',3':4,5]pyrimido[6,1-b]quinazolin-7(3H)-one HCl salt

HRID 1014566Notes

Reaction equation

HRID 1014566 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:24]=2[C:25]([OH:27])=O)[C:5]2[CH:10]=[C:9]([CH3:11])[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1.C(Cl)(=O)C(Cl)=O.ClCCl>C1COCC1.CN(C=O)C>[ClH:1].[Cl:1][C:2]1[N:3]2[C:4](=[N:22][C:23]3[C:24]([C:25]2=[O:27])=[C:28]([F:32])[CH:29]=[CH:30][CH:31]=3)[C:5]2[CH:10]=[C:9]([CH3:11])[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 594418482-({2-chloro-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid

Product 1

HCID 673158975-chloro-8-fluoro,2-methyl-3-[(4-methylphenyl)sulfonyl]pyrrolo[2',3':4,5]pyrimido[6,1-b]quinazolin-7(3H)-one HCl saltYield 186.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-({2-chloro-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid (439 mg, 0.924 mmol) in THF (15 mL) and DMF (few drops) was added 2M oxalyl chloride solution in dichloromethane (0.56 mL, 1.13 mmol) dropwise. After ˜15 min, LCMS analysis shows reaction complete so reaction mixture was cooled in an ice bath and filtered via a buchner funnell and thet solid was washed with THF and dried under reduced pressure to afford 5-chloro-8-fluoro-2-methyl-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one HCl salt (423 mg, 0.86 mmol) as a yellow solid. ESIMS (M+H)+=457.

Workup

  1. customreaction
  2. customcomplete so reaction mixture
  3. temperaturewas cooled in an ice bath
  4. filtrationfiltered via a buchner funnell
  5. washthet solid was washed with THF
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-e9151e08fa234d55bb431dd67b3eb637
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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