Oxalyl chloride → 5-chloro-8,10-difluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2',3':4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chloride

HRID 1014477Notes

Reaction equation

HRID 1014477 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[C:23]=2[C:24]([OH:26])=O)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.C(Cl)(=O)C(Cl)=O>C1COCC1.CN(C=O)C>[ClH:1].[Cl:1][C:2]1[N:3]2[C:4](=[N:21][C:22]3[C:23]([C:24]2=[O:26])=[C:27]([F:32])[CH:28]=[C:29]([F:31])[CH:30]=3)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 594416592-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-4,6-difluorobenzoic acid

Product 1

HCID 673172765-chloro-8,10-difluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2',3':4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chlorideYield 190%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

An opaque solution of 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-4,6-difluorobenzoic acid (5.3 g, 11.07 mmol) in THF (300 mL) was treated with a few drops of DMF, followed by oxalyl chloride (1M in CH2Cl2, 22.14 mL, 44.3 mmol). The reaction mixture was stirred for 1 h, then placed in an ice-bath for 2 h. The resulting slurry was filtered, the solid washed with CH2Cl2 to obtain 5-chloro-8,10-difluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chloride as a white solid (5.23 g, 95%). 1H NMR (400 MHz, THF-d6) δ ppm 2.41 (s, 3H), 6.97-7.12 (m, 2H), 7.12-7.24 (m, 1H), 7.44 (d, J=8.24 Hz, 2H), 7.68 (d, J=3.66 Hz, 1H), 8.11 (d, J=8.42 Hz, 2H); ESIMS (M+H)+=460.94.

Workup

  1. waitplaced in an ice-bath for 2 h
  2. filtrationThe resulting slurry was filtered
  3. washthe solid washed with CH2Cl2

Sources & evidence

ORD record
ord-9e7370f6ee374214886d8ebcfb62a2b0
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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