Pyridine → HCID 86702951, compound

HRID 1505499Notes

Reaction equation

HRID 1505499 reaction equation
[F:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11]1[C:16]([C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[N:19]=[CH:20][N:21]3[CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:15][CH:14]=[CH:13][N:12]=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[C:35]([F:43])[CH:34]=1.N1C=CC=CC=1>ClCCl>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([S:39]([NH:8][C:7]2[CH:6]=[CH:5][C:4]([F:9])=[C:3]([NH:10][C:11]3[C:16]([C:17]4[N:25]=[CH:24][N:23]=[C:22]5[C:18]=4[N:19]=[CH:20][N:21]5[CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][O:27]4)=[CH:15][CH:14]=[CH:13][N:12]=3)[C:2]=2[F:1])(=[O:40])=[O:41])=[C:35]([F:43])[CH:34]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27788604-Chloro-2-fluorobenzene-1-sulfonyl chlorideHCID 867029472,6-difluoro-N1-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)benzene-1,3-diamine

Product 1

HCID 86702951HCID 86702951, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

The 2,6-difluoro-N1-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)benzene-1,3-diamine (20 mg, 0.047 mmol) prepared at Step 9 was added and dissolved into dichloromethane solvent. 4-chloro-2-fluorobenzenesulfonyl chloride (16 mg, 0.052 mmol) and pyridine (8 uL, 0.094 mmol) were added into the reaction solution and stirred at 50° C. for 2 hours. After the reaction, the reactant was washed with 1N aqueous hydrochloric acid solution and salt water. After extraction with dichloromethane, the organic layer was dried with sulfuric anhydride magnesium and vacuum concentrated, and then refined by means of column chromatography, so that 26 mg of the target compound, 4-chloro-N-(2,4-difluoro-3-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)phenyl)-2-fluorobenzenesulfonamide (percentage yield: 91%), was obtained.

Workup

  1. additionwas added
  2. customAfter the reaction
  3. washthe reactant was washed with 1N aqueous hydrochloric acid solution and salt water
  4. extractionAfter extraction with dichloromethane
  5. dry with materialthe organic layer was dried with sulfuric anhydride magnesium and vacuum
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3fb54f6d20d64307904e06946bb9636a
Source dataset
uspto-grants-2015_12
Patent number
US09216981B2

Reaction notes

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