Diisopropylamine → HCID 69059056, compound

HRID 1821591Notes

Reaction equation

HRID 1821591 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[N:14][C:15]=2[NH:17][CH2:18][CH:19]([OH:21])[CH3:20])[N:10]([CH2:31][OH:32])[N:9]=1.C(NC(C)C)(C)C.CN(C1C=CC=CN=1)C.[C:49]1(=[O:55])[O:54][C:52](=[O:53])[CH2:51][CH2:50]1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[N:14][C:15]=2[NH:17][CH2:18][CH:19]([OH:21])[CH3:20])[N:10]([CH2:31][O:32][C:49](=[O:55])[CH2:50][CH2:51][C:52]([OH:54])=[O:53])[N:9]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 69059592HCID 69059592, compound

Product 1

HCID 69059056HCID 69059056, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[3-(2-Chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1-hydroxymethyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol (2.0 g, 4.3 mmol) was dissolved in 80 mL THF, and diisopropylamine (0.78 g, 5.6 mmol), dimethyamino pyridine (52 mg, 0.4 mmol) and succinic anhydride (703 mg, 7.0 mmol) were added while stirring at room temperature. The reaction mixture was stirred for 16 hours at room temperature, then partitioned between water and ethyl acetate, and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was dissolved in EtOAc and purified by flash chromatography (silica gel, hexanes/EtOAc 1:1 to EtOAc/AcOH 100:1) to give 0.62 g of succinic acid mono-[3-(2-chloro-phenyl)-6-(2,4-difluoro-phenoxy)-4-(2-hydroxy-propylamino)-pyrazolo[3,4-d]pyrimidin-1-ylmethyl]ester, MS (M+H)=562

Workup

  1. stirringThe reaction mixture was stirred for 16 hours at room temperature
  2. custompartitioned between water and ethyl acetate
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in EtOAc
  7. custompurified by flash chromatography (silica gel, hexanes/EtOAc 1:1 to EtOAc/AcOH 100:1)

Sources & evidence

ORD record
ord-40abd29e8e544cc097a3af46ca02b5b2
Source dataset
uspto-grants-2009_10
Patent number
US07608603B2

Reaction notes

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