Hydrochloric Acid → HCID 178433095, compound

HRID 457557Notes

Reaction equation

HRID 457557 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([C:23]4[C:24]([O:30]C)=[N:25][CH:26]=[CH:27][C:28]=4I)[NH:20]3)=[C:16]([CH3:32])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:33].C(N(CC)CC)C.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([C:23]4[C:24](=[O:30])[NH:25][CH:26]=[CH:27][C:28]=4[Cl:33])[NH:20]3)=[C:16]([CH3:32])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 178494185HCID 178494185, compound

Product 1

HCID 178433095HCID 178433095, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-[8-(4-iodo-2-methoxy-pyridin-3-yl)-6-methyl-9H-purin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (1.4 g, 2.54 mmol) in glacial acetic acid (30 mL) was added 11.6 M HCl (30 mL). The reaction mixture was stirred at 75° C. for 6 hours in a sealed tube and concentrated. The residue was dissolved in CH2Cl2 (250 mL) followed by the addition of triethylamine (2.78 mL, 20 mmol). The solution was cooled to 0° C. and di t-butyl dicarbonate (573 mg, 2.63 mmol) was added. The reaction mixture was stirred at 23° C. for 2 hours, poured on saturated NaHCO3 solution and extracted with CH2Cl2 (3×200 mL). The combined organic layers, were dried over MgSO4 and concentrated to give the title compound as a yellow solid. (0.691 g, 62%). HPLC 93%; LCMS (+ESI, M+H+) m/z 446; IR (KBr, cm−1) 3431, 2974, 1700, 1506, 1229; 1H NMR (400 MHz, DMSO+D2O) δ 7.64 (d, J=7.0 Hz, 0.7H), 7.32 (d, J=7.0 Hz, 0.3H), 6.89 (d, J=7.0 Hz, 0.3H), 6.59 (d, J=7.0 Hz, 0.7H), 3.75 (br s, 4H), 3.45 (br s, 4H), 2.60 (s, 3H), 1.45 (s, 9H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in CH2Cl2 (250 mL)
  3. temperatureThe solution was cooled to 0° C.
  4. stirringThe reaction mixture was stirred at 23° C. for 2 hours
  5. extractionextracted with CH2Cl2 (3×200 mL)
  6. dry with materialThe combined organic layers, were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2746c3018e184ea38154acb5108b0276
Source dataset
uspto-grants-2007_03
Patent number
US07189716B2

Reaction notes

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