Water → HCID 178463537, compound

HRID 1192536Notes

Reaction equation

HRID 1192536 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:16]([CH:26]([NH:28][C:29]3[N:37]=[CH:36][N:35]=[C:34]4[C:30]=3[N:31]=[CH:32][NH:33]4)[CH3:27])=[CH:17][C:18]([Cl:25])=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.F[Si-2](F)(F)(F)(F)F.[H+].[H+].O.[OH-].[Na+]>C(#N)C>[Cl:25][C:18]1[CH:17]=[C:16]([CH:26]([NH:28][C:29]2[N:37]=[CH:36][N:35]=[C:34]3[C:30]=2[N:31]=[CH:32][NH:33]3)[CH3:27])[C:15]([N:12]2[CH2:11][CH2:10][CH:9]([OH:8])[CH2:14][CH2:13]2)=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 178463538HCID 178463538, compound

Product 1

HCID 178463537HCID 178463537, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of N-{1-[8-(4-{[tert-butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethyl}-9H-purin-6-amine (0.200 g, 0.372 mmol) in acetonitrile (1 mL) was added 2.0 M fluorosilicic acid in water (0.929 mL, 1.86 mmol). The reaction was stirred at room temperature for 30 minutes, then neutralized with aq. sodium hydroxide and extracted with dichloromethane. The extracts were combined and evaporated to dryness. The residue was purified on a RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min) to give the desired product as the free base. LCMS calculated for C21H23ClN7O (M+H)+: m/z=424.2; Found: 424.1. 1H NMR (DMSO-d6, 400 MHz) δ 12.89 (1H, s), 8.95 (1H, m), 8.44 (1H, m), 8.27 (1H, m), 8.11 (1H, s), 8.01 (1H, s), 7.99 (1H, s), 7.58 (1H, dd, J=8.4 and 4.0 Hz), 6.35 (1H, br s), 4.67 (1H, m), 4.01 (1H, m), 3.76 (1H, m), 3.61 (1H, m), 2.78 (1H, m), 1.90 (2H, m), 1.79˜1.61 (3H, m), 1.52 (3H, d, J=7.2 Hz) ppm.

Workup

  1. extractionextracted with dichloromethane
  2. customevaporated to dryness
  3. customThe residue was purified on a RP-HPLC (XBridge C18 column
  4. washeluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-f1d44110b077469d9bc37c97cb16c381
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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