Water → HCID 59400113, compound

HRID 2389535Notes

Reaction equation

HRID 2389535 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH:7]([NH2:15])[CH2:6]1.Cl[C:22]1[N:27]=[C:26]([NH2:28])[N:25]=[C:24]2[NH:29][N:30]=[CH:31][C:23]=12.C(N(C(C)C)CC)(C)C.O>CC(N(C)C)=O>[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH:7]([NH:15][C:22]2[N:27]=[C:26]([NH2:28])[N:25]=[C:24]3[NH:29][N:30]=[CH:31][C:23]=23)[CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amineHCID 59400153HCID 59400153, compound

Product 1

HCID 59400113HCID 59400113, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1-(2,4-difluorobenzyl)-1,2,3,4-tetrahydroquinolin-3-amine, 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine (200 mg, 1.2 mmol) and diisopropylethylamine (1 mL) in dimethylacetamide (6 mL) was stirred at 126° C. for 20 hours. After cooling to room temperature, water (15 mL) was added and the mixture extracted with ethyl acetate (3×15 mL). The combined organics were dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (100% ethyl acetate) to provide N4-(1-(2,4-difluorobenzyl)-1,2,3,4-tetrahydroquinolin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine as a light yellow solid (160 mg). M.p.=110-114° C. 1H NMR (DMSO-d6, 400 MHz) δ 12.43 (s, 1H), 7.83 (s, 1H), 7.62 (d, J=6.0 Hz, 1H), 7.34-7.21 (m, 2H), 7.03-6.95 (m, 3H), 6.58-6.54 (m, 2H), 6.00 (s, 2H), 4.66 (br, 1H), 4.54 (m, 2H), 3.55-3.51 (m, 1H), 3.39-3.29 (m, 1H), 3.09-3.04 (m, 1H), 2.89-2.81 (m, 1H). LCMS m/e 408 (M+1).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×15 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel (100% ethyl acetate)

Sources & evidence

ORD record
ord-153fac7840764c26af38ac28072140d6
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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