Water → HCID 59400122, compound

HRID 2389555Notes

Reaction equation

HRID 2389555 reaction equation
[C:1]1([S:7]([N:10]2[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:23]1[N:28]=[C:27]([NH2:29])[N:26]=[C:25]2[NH:30][N:31]=[CH:32][C:24]=12.C(N(C(C)C)CC)(C)C.O>CC(N(C)C)=O>[C:1]1([S:7]([N:10]2[CH2:16][CH2:15][CH:14]([NH:17][C:23]3[N:28]=[C:27]([NH2:29])[N:26]=[C:25]4[NH:30][N:31]=[CH:32][C:24]=34)[CH2:13][C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]2=3)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amineHCID 59400108HCID 59400108, compound

Product 1

HCID 59400122HCID 59400122, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-amine in anhydrous dimethylacetamide (1 mL) was added 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine (135 mg, 1.0 mmol) and diisopropylethylamine (0.4 mL, 2.30 mmol). The mixture was stirred at 120° C. for 20 hours. After cooling to room temperature the mixture was poured into water (10 ml) and extracted with ethyl acetate (3×10 ml). The combined organics were dried over sodium sulfate and concentrated to a residue which was purified by reverse phase chromatography on a preparative LC/UV/MS system using a mass triggered fractionation. Compounds were eluted from the HPLC column (Maccel 120-10-C18 SH 10 μm 20 mmID×50 mm) at 88 ml/min with 5-95 acetonitrile/water gradient using 0.1% TFA as modifier to yield N4-(1-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (13.4 mg).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with ethyl acetate (3×10 ml)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. concentrationconcentrated to a residue which
  5. customwas purified by reverse phase chromatography on a preparative LC/UV/MS system
  6. washCompounds were eluted from the HPLC column (Maccel 120-10-C18 SH 10 μm 20 mmID×50 mm) at 88 ml/min with 5-95 acetonitrile/water gradient

Sources & evidence

ORD record
ord-2be8c01654be493b8bd956cc079bb0f5
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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