Water → HCID 59400215, compound

HRID 2389560Notes

Reaction equation

HRID 2389560 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:23])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:3]1.Cl[C:32]1[N:37]=[C:36]([NH2:38])[N:35]=[C:34]2[NH:39][N:40]=[CH:41][C:33]=12.C(N(C(C)C)CC)(C)C.O>CC(N(C)C)=O>[NH2:38][C:36]1[N:35]=[C:34]2[NH:39][N:40]=[CH:41][C:33]2=[C:32]([NH:1][CH:2]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])=[CH:17][CH:16]=3)(=[O:13])=[O:14])[CH2:3]2)[N:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amineHCID 59400161HCID 59400161, compound

Product 1

HCID 59400215HCID 59400215, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(4-(3-amino-3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl)-3-phenylurea in dimethyl acetamide (1 mL) was added 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine (135 mg, 1.0 mmol) and diisopropylethylamine (0.4 mL, 0.30 g, 2.30 mmol). The reaction 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 give a residue that 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 1-(4-(3-(6-amino-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)-3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl)-3-phenylurea (47.6 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
  5. customto give a residue that
  6. customwas purified by reverse phase chromatography on a preparative LC/UV/MS system
  7. 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-4d9cd876d6ce4bf3b3452495c6e8e661
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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