Oxalyl chloride → HCID 25150091, compound

HRID 1014528Notes

Reaction equation

HRID 1014528 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][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])=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)(=[O:12])=[O:13])[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 25150196HCID 25150196, compound

Product 1

HCID 25150091HCID 25150091, compoundYield 189.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoic acid (28 g, 63.2 mmol) in THF (500 mL) was treated with 2 drops of DMF and oxalyl chloride (8.30 mL, 95 mmol), and was stirred at rt for 3 h. The resulting slurry was filtered to obtain 5-chloro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chloride as a yellow solid (27.67 g, 95%). 1H NMR (free base) (400 MHz, DMSO-d6) δ ppm 2.37 (s, 3H), 7.07 (d, 4.21 Hz, 1H), 7.34 (d, J=4.21 Hz, 1H), 7.47 (d, 8.06 Hz, 2H), 7.53-7.63 (m, 1H), 7.78-7.90 (m, 1H), 8.00 (d, J=8.42 Hz, 2H), 8.18 (dd, J=7.78 Hz, 1.74 Hz, 1H), 9.28 (d, J=8.42 Hz, 1H); ESIMS (M+H)+=424.97.

Workup

  1. filtrationThe resulting slurry was filtered

Sources & evidence

ORD record
ord-611ea66079024cd08c43b021493d3405
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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