Oxalyl chloride → 8-bromo-5-chloro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2',3':4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chloride

HRID 1014514Notes

Reaction equation

HRID 1014514 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[C:13]3[CH:21]=[CH:20][N:19]([S:22]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)(=[O:24])=[O:23])[C:14]=3[N:15]=[C:16]([Cl:18])[N:17]=2)[C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O>C1COCC1>[ClH:18].[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:6])[N:17]1[C:16]([Cl:18])=[N:15][C:14]3[N:19]([S:22]([C:25]4[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=4)(=[O:23])=[O:24])[CH:20]=[CH:21][C:13]=3[C:12]1=[N:11]2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 251499842-bromo-6-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoic acid

Product 1

HCID 673171988-bromo-5-chloro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2',3':4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-6-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoic acid (1.5 g, 2.87 mmol) in THF(200 ml) was added oxalyl chloride (4.31 ml, 8.62 mmol, 2.0M DCM) and the reaction was stirred at rt for 1 hr. The reaction was concentrated on rotovap, redissolved in THF, evaporated again, and high vacced prior to next step to yield 8-bromo-5-chloro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chloride (1.3 g, 90%). ESIMS (M+H)+=503.

Workup

  1. concentrationThe reaction was concentrated on rotovap
  2. dissolutionredissolved in THF
  3. customevaporated again

Sources & evidence

ORD record
ord-70a87aac952f4a50ac563d7535765889
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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