Diisopropylethylamine → HCID 59400116, compound

HRID 2389545Notes

Reaction equation

HRID 2389545 reaction equation
OC(C(F)(F)F)=O.[C:8]1([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH:16]([NH2:24])[CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:26]1[N:31]=[C:30]([NH2:32])[N:29]=[C:28]2[NH:33][N:34]=[CH:35][C:27]=12.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O.O>[C:8]1([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH:16]([NH:24][C:26]3[N:31]=[C:30]([NH2:32])[N:29]=[C:28]4[NH:33][N:34]=[CH:35][C:27]=34)[CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amineHCID 86643200HCID 86643200, compound

Product 1

HCID 59400116HCID 59400116, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 1-phenyl-1,2,3,4-tetrahydroquinolin-3-amine TFA salt (325 mg, 0.96 mmol) and 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine (325 mg, 1.92 mmol) in dimethylacetamide (4 mL) was treated with diisopropylethylamine (0.5 ml, 3 eq). The mixture was heated at 120° C. for 20 hours. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic layer was further washed with brine and dried over anhydrous sodium sulfate. The residue was purified by flash column (eluted with ethyl acetate:hexane: 40% to 100% ethyl acetate) to give N4-(1-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine as a yellow a solid (240 mg). M.p.=88-92° C. 1H NMR (DMSO) 400 MHz δ 12.39 (s, 1H), 7.80 (s, br, 1H), 7.64 (d, J=6.8 Hz, 1H), 7.35-7.25 (m, 2H), 7.23 (m, 2H), 7.07 (m, 2H), 6.92 (m, 1H), 6.69 (m, 2H), 5.96 (s, 1H), 4.66 (s, br, 1H), 3.85 (m, 1H), 3.47 (m, 1H), 3.14 (dd, J=5.6 and 10.0 Hz, 1H), 2.88 (m, 1H). LCMS m/e 348 (M+H).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was further washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue was purified by flash column (eluted with ethyl acetate:hexane: 40% to 100% ethyl acetate)

Sources & evidence

ORD record
ord-acf9f992a76d466794da6ab2ecd0193e
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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