Diisopropylethylamine → 2-({2-chloro-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid

HRID 1014565Notes

Reaction equation

HRID 1014565 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[C:9]([CH3:11])[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].C(N(C(C)C)CC)(C)C>C(O)(C)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[CH:10]=[C:9]([CH3:11])[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 81531DiisopropylethylamineHCID 5211422-Amino-6-fluorobenzoic acidHCID 583989172,4-dichloro-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 594418482-({2-chloro-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acidYield 66%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 2,4-dichloro-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (500 mg, 1.40 mmol) and 2-amino-6-fluorobenzoic acid (218 mg, 1.40 mmol) in isopropanol (15 mL) was added diisopropylethylamine (907 mg, 7.02 mmol) and the mixture was heated at 85° C. for ˜72 h. The reaction was diluted with EtOAc (100 ml) and washed with a solution of 1N HCl, a saturated solution of sodium bicarbonate and a saturated solution of NaCl. Solid began to crash out on addition of brine. Ether was added to force everything out of solution and also water was added to ensure NaCl was all in solution. The solids were filtered and dried under reduced pressure to afford 2-({2-chloro-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid (439 mg, 0.924 mmol) as a pale yellow solid. ESIMS (M+H)+=475.

Workup

  1. washwashed with a solution of 1N HCl
  2. additionto crash out on addition of brine
  3. additionEther was added
  4. additionwas added
  5. filtrationThe solids were filtered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-b062c54d9e0d46028f4c5463e6cbb81b
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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