Dimethylformamide → HCID 67316036, compound

HRID 1014550Notes

Reaction equation

HRID 1014550 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[C:10]([F:11])=[CH:9][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.CN(C=O)C.C(Cl)(=O)C(Cl)=O>C1COCC1>[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[C:10]([F:11])=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:13])=[O:14])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 59441796HCID 59441796, compound

Product 1

HCID 67316036HCID 67316036, compoundYield 164.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 2-({2-chloro-5-fluoro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid (0.68 g, 1.420 mmol) in THF (100 mL) was treated with a drop of DMF, followed by a solution of oxalyl chloride (2M in CH2Cl2, 2.84 mL, 5.48 mmol). After 30 min Et20 (50 mL) was added. The resulting slurry was filtered and the solids were washed with Et2O, then dried in vacuum to obtain 5-chloro-1,8-difluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chloride as a pale yellow solid (580 mg, 82%). 1H NMR (400 MHz, THF-d8) δ ppm 2.41 (s, 3H), 7.14 (dd, J=10.07, 8.61 Hz, 1H), 7.45 (d, 8.06 Hz, 3H), 7.56 (d, J=2.56 Hz, 1H), 7.69-7.83 (m, 1H), 8.09 (d, J=8.42 Hz, 2H), 10.84 (br s, 1H); ESIMS (M+H)+=460.98.

Workup

  1. additionAfter 30 min Et20 (50 mL) was added
  2. filtrationThe resulting slurry was filtered
  3. washthe solids were washed with Et2O
  4. customdried in vacuum

Sources & evidence

ORD record
ord-2deb1af6d3874a5db30b53e17edc8a79
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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