Trifluoroacetic acid → HCID 178492161, compound

HRID 1811877Notes

Reaction equation

HRID 1811877 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[CH:21][C:20]([CH2:23][N:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)=[CH:19][C:18]=2[C:37]2[N:45]=[C:44]([CH3:46])[N:43]=[C:42]3[C:38]=2[N:39]=[CH:40][N:41]3C2CCCCO2)=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:8][O:9][C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17]2[C:18]([C:37]3[N:45]=[C:44]([CH3:46])[N:43]=[C:42]4[C:38]=3[N:39]=[CH:40][NH:41]4)=[CH:19][C:20]([CH2:23][N:24]3[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]3)=[CH:21][N:22]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66600098tert-butyl 4-((6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 178492161HCID 178492161, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2.00 mL) was added to a stirred mixture of tert-butyl 4-((6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)methyl)piperazine-1-carboxylate (112 mg, 0.182 mmol) in DCM (2.00 mL) and the mixture was stirred at room temperature for 1 h. The mixture was concentrated and re-diluted with DCM, NaHCO3(aq) and water (10 mL each). The separated aqueous layer was extracted with DCM (4×20 mL) and the combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified by flash column chromatography (DCM to 10% MeOH in DCM) to give N-(6-methoxypyridin-3-yl)-3-(2-methyl-9H-purin-6-yl)-5-(piperazin-1-ylmethyl)pyridin-2-amine (15 mg, 0.035 mmol, 19.11% yield) as a yellow solid. LCMS (API-ES) m/z 432 (M+H)+; 1H NMR (400 MHz, d6-DMSO) δ 12.63 (br. s., 1H) 9.69 (br. s., 1H) 8.60 (br. s., 1H) 8.54 (br. s., 1H) 7.86-8.30 (m, 3H) 6.85 (d, J=9.19 Hz, 1H) 3.85 (s, 3H) 3.52 (br. s., 2H) 2.90 (br. s., 4H) 2.85 (br. s., 3H) 2.37-2.49 (m, 4H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionre-diluted with DCM, NaHCO3(aq) and water (10 mL each)
  3. extractionThe separated aqueous layer was extracted with DCM (4×20 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (DCM to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-bfc3f3170349439d95c51c48a7f444e8
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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