HCID 44479178, compound → HCID 86702968, compound

HRID 1505529Notes

Reaction equation

HRID 1505529 reaction equation
[NH2:1][C:2]1[C:3]([F:19])=[C:4]([NH:9][S:10]([C:13]2[N:14]=[CH:15][N:16]([CH3:18])[CH:17]=2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].F[C:21]1[C:26]([C:27]2[N:35]=[CH:34][N:33]=[C:32]3[C:28]=2[N:29]=[CH:30][N:31]3[CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)=[CH:25][CH:24]=[CH:23][N:22]=1>O>[F:19][C:3]1[C:2]([NH:1][C:21]2[C:26]([C:27]3[N:35]=[CH:34][N:33]=[C:32]4[C:28]=3[N:29]=[CH:30][N:31]4[CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)=[CH:25][CH:24]=[CH:23][N:22]=2)=[C:7]([F:8])[CH:6]=[CH:5][C:4]=1[NH:9][S:10]([C:13]1[N:14]=[CH:15][N:16]([CH3:18])[CH:17]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 44479178HCID 44479178, compoundHCID 86702965HCID 86702965, compound

Product 1

HCID 86702968HCID 86702968, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The N-(3-amino-2,4-difluorophenyl)-1-methyl-1H-imidazole-4-sulfonamide (45 mg, 0.16 mmol) prepared at Step 5 and the 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (43 mg, 0.14 mmol) prepared at Step 7 were added and dissolved, and lithium (bistrimethylsilyl) amide (1.0M solution in THF) was applied slowly at 0° C. After stirring the reactant at room temperature for 1 hour, completing the reaction, pouring water, and extracting with ethylacetate, the organic layer was dried with sulfuric anhydride magnesium and vacuum concentrated, and then refined by means of column chromatography, so that 65 mg of the target compound, N-(2,4-difluoro-3-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)phenyl)-1-methyl-1H-imidazole-4-sulfonamide (percentage yield: 82%), was obtained.

Workup

  1. additionwere added
  2. dissolutiondissolved
  3. customwas applied slowly at 0° C
  4. customthe reaction
  5. extractionextracting with ethylacetate
  6. dry with materialthe organic layer was dried with sulfuric anhydride magnesium and vacuum
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a76149d22874f379ef538bf3aa0d5b9
Source dataset
uspto-grants-2015_12
Patent number
US09216981B2

Reaction notes

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