Triethylamine → HCID 178503431, compound

HRID 1809689Notes

Reaction equation

HRID 1809689 reaction equation
Cl[C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[C:5]2=[CH:4][N:3]=1.[NH2:19][C@@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]1.C(N(CC)CC)C>CC(O)C>[C:29]([O:28][C:27](=[O:33])[NH:26][CH:23]1[CH2:22][CH2:21][CH:20]([NH:19][C:2]2[N:7]=[C:6]3[NH:8][N:9]=[C:10]([C:11]4[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=4)[C:5]3=[CH:4][N:3]=2)[CH2:25][CH2:24]1)([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 178418966HCID 178418966, compoundHCID 178503430HCID 178503430, compound

Product 1

HCID 178503431HCID 178503431, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 6-chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine (from Example 7 supra) (500 mg, 1.80 mmol) in 2-propanol (50 mL) was added cis-tert-butyl 4-aminocyclohexylcarbamate (425 mg, 1.98 mmol) followed by triethylamine (200 mg, 1.98 mmol). The reaction mixture was stirred at reflux for 15 hours and the solvent was then removed under reduced pressure. The residue was suspended in dichloromethane (50 mL), washed with water (3×25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford {4-[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester. (Yield 550 mg, 67.1%).

Workup

  1. temperatureat reflux for 15 hours
  2. customthe solvent was then removed under reduced pressure
  3. washwashed with water (3×25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57cfa8ceb498435ba5806a4c27ba3f9b
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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