HCID 178482342, compound → HCID 178482341, compound

HRID 928235Notes

Reaction equation

HRID 928235 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]2[N:9]([CH2:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([NH:25]C(=O)OC(C)(C)C)[CH2:21][CH2:20]3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]2=[CH:5][N:4]=1>C(Cl)Cl>[NH2:25][C@H:22]1[CH2:21][CH2:20][C@H:19]([CH2:18][N:9]2[C:7]3=[N:8][C:3]([NH:2][CH3:1])=[N:4][CH:5]=[C:6]3[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10]2)[CH2:24][CH2:23]1

Participants

3

Reactant 1

HCID 178482342HCID 178482342, compound

Product 1

HCID 178482341HCID 178482341, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl trans-4-((6-(methylamino)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate (0.082 g, 0.19 mmol) in methylene chloride (3 mL) was added trifluoroacidic acid (0.60 mL). The reaction mixture was stirred at room temperature for 2 h, concentrated and basified by a 7.0 M aqueous solution of ammonia to pH 12. After evaporation, the residue was purified by Isco to provide 1-((trans-4-aminocyclohexyl)methyl)-N-methyl-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine (UNC00000545A) (0.051 g, 80%) as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.94 (s, 1H), 7.94-7.83 (m, 2H), 7.55-7.44 (m, 2H), 7.44-7.36 (m, 1H), 4.16 (d, J=7.5 Hz, 2H), 3.06-2.91 (m, 1H), 2.99 (s, 3H), 2.13-1.93 (m, 3H), 1.78 (d, J=12.7 Hz, 2H), 1.45-1.14 (m, 4H); 13C NMR (100 MHz, CD3OD) δ 162.87, 157.72, 154.93, 145.73, 133.64, 130.01, 129.95, 127.97, 52.28, 51.32, 49.64, 49.43, 49.21, 49.00, 48.79, 48.57, 48.36, 38.38, 31.91, 29.71, 28.52; MS m/z 337.3 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customAfter evaporation
  3. customthe residue was purified by Isco

Sources & evidence

ORD record
ord-80ae4725a85b48e08ad25566e044f3b1
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

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