Hydrochloric Acid → HCID 59441796, compound

HRID 1014549Notes

Reaction equation

HRID 1014549 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[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.[NH2:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:25]=1[C:26]([OH:28])=[O:27].Cl>CC(O)C.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:23][C:24]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:25]=2[C:26]([OH:28])=[O:27])[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

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5211422-Amino-6-fluorobenzoic acidHCID 59441641HCID 59441641, compound

Product 1

HCID 59441796HCID 59441796, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 2,4-dichloro-5-fluoro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (1.250 g, 3.47 mmol) DIPEA (3.03 mL, 17.35 mmol) and 2-amino-6-fluorobenzoic acid (0.646 g, 4.16 mmol) in iPrOH (30 mL) was heated at 90° C. for 3 h. The resulting mixture was allowed to cool to rt and diluted with EtOAc (100 mL) and a 1N HCl solution (100 mL). The organic layer was washed with a saturated NaHCO3 solution (100 mL) and a saturated NaCl solution (100 mL). The organic layer was diluted with Et2O and the resulting slurry filtered. The solids were washed with Et2O and dried in vacuum to afford 2-({2-chloro-5-fluoro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid (0.69 g, 41%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.38 (s, 3H), 6.71-6.87 (m, 1H), 7.21-7.36 (m, 1H), 7.48 (d, J=8.06 Hz, 2H), 7.76 (s, 1H), 7.96 (d, J=8.42 Hz, 2H), 8.26 (d, J=8.61 Hz, 1H).

Workup

  1. washThe organic layer was washed with a saturated NaHCO3 solution (100 mL)
  2. additionThe organic layer was diluted with Et2O
  3. filtrationthe resulting slurry filtered
  4. washThe solids were washed with Et2O
  5. customdried in vacuum

Sources & evidence

ORD record
ord-8ec8976af7d34848ae2d8a88869f34bf
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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