Acetic Acid → HCID 23154919, compound

HRID 1912877Notes

Reaction equation

HRID 1912877 reaction equation
C(O[C:6](=O)[N:7](C)[C:8]1[N:16]=[CH:15][N:14]=[C:13]2[C:9]=1[N:10]=[CH:11][N:12]2[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH:34]=O)=[C:29]([C:36]([F:39])([F:38])[F:37])[CH:28]=2)=[O:25])=[CH:19][CH:18]=1)(C)(C)C.C(O)(=O)C.[CH3:46][NH:47][CH3:48].C([BH3-])#N.[Na+]>C(O)C>[CH3:46][N:47]([CH3:48])[CH2:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([NH:26][C:24]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([N:12]3[CH:11]=[N:10][C:9]4[C:13]3=[N:14][CH:15]=[N:16][C:8]=4[NH:7][CH3:6])=[CH:22][CH:21]=2)=[O:25])=[CH:28][C:29]=1[C:36]([F:38])([F:37])[F:39]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 59725889HCID 59725889, compound

Product 1

HCID 23154919HCID 23154919, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 1 mL of ethanol, 25 mg (0.04 mmol) of methyl-[9-(4-{3-[4-(2-oxoethyl)-3-(trifluoromethyl)phenyl]ureido}-phenyl)-9H-purin-6-yl]-carbamic acid tert-butyl ester was dissolved, and 10 μL of acetic acid and 0.1 mL (0.20 mmol) of 2N dimethylamine were added thereto and the mixture solution was stirred at room temperature for 30 minutes. Furthermore, 7 mg (0.11 mmol) of sodium cyanoborohydride was added to the obtained solution and the mixture solution was stirred at room temperature for one hour. The reaction solution was concentrated and to the residue, 0.5 mL of trifluoroacetic acid was added and the mixture was stirred at room temperature for one hour. The reaction solution was concentrated, and a target product was obtained by a reversed phase HPLC (a product of Wako Pure Chemical, Combi ODS, 28 mm×50 mm, 0.05% acetonitrile-water, 30 mL/min). The fraction containing the target product was concentrated, and then dissolved in methanol and neutralized by addition of amino silica gel R 66030 B (a product of Silicycle), and then a solid was removed by filtration and the filtrate was concentrated to obtain 15 mg (52%) of a title compound.

Workup

  1. stirringthe mixture solution was stirred at room temperature for one hour
  2. concentrationThe reaction solution was concentrated and to the residue, 0.5 mL of trifluoroacetic acid
  3. additionwas added
  4. stirringthe mixture was stirred at room temperature for one hour
  5. concentrationThe reaction solution was concentrated
  6. customa target product was obtained by a reversed phase HPLC (a product of Wako Pure Chemical, Combi ODS, 28 mm×50 mm, 0.05% acetonitrile-water, 30 mL/min)
  7. additionThe fraction containing the target product
  8. concentrationwas concentrated
  9. dissolutiondissolved in methanol
  10. additionneutralized by addition of amino silica gel R 66030 B (a product of Silicycle), and then a solid
  11. customwas removed by filtration
  12. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fbe736d4353a4f1fb96e43b52825090e
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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