Hydrochloric Acid → HCID 178463546, compound

HRID 717843Notes

Reaction equation

HRID 717843 reaction equation
[NH2:1][CH:2]([C:4]1[CH:5]=[C:6]([Cl:24])[C:7]2[N:8]([CH:21]=[N:22][CH:23]=2)[C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:20])[CH2:17][C:18]#[N:19])[CH2:12][CH2:11]1)[CH3:3].Br[C:26]1[N:34]=[CH:33][N:32]=[C:31]2[C:27]=1[N:28]=[CH:29][N:30]2C1CCCCO1.C(N(CC)C(C)C)(C)C.Cl.O1CCOCC1>C(O)C>[Cl:24][C:6]1[C:7]2[N:8]([CH:21]=[N:22][CH:23]=2)[C:9]([N:10]2[CH2:11][CH2:12][N:13]([C:16](=[O:20])[CH2:17][C:18]#[N:19])[CH2:14][CH2:15]2)=[C:4]([CH:2]([NH:1][C:26]2[N:34]=[CH:33][N:32]=[C:31]3[C:27]=2[N:28]=[CH:29][NH:30]3)[CH3:3])[CH:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 81531DiisopropylethylamineHCID 583686166-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purineHCID 58515959HCID 58515959, compound

Product 1

HCID 178463546HCID 178463546, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-{4-[6-(1-aminoethyl)-8-chloroimidazo[1,5-a]pyridine-5-yl}piperazin-1-yl]-3-oxopropanenitrile (18 mg, 0.052 mmol), 6-bromo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (29 mg, 0.10 mmol) and N,N-diisopropylethylamine (27 μL, 0.16 mmol) in ethanol (1.0 mL) was heated at 110° C. overnight. The mixture was evaporated and a 4 M solution of hydrogen chloride in 1,4-dioxane (1.0 mL, 4.0 mmol) was added. The mixture was evaporated and a 4 M solution of hydrogen chloride in 1,4-dioxane (1.0 mL, 4.0 mmol) was added. The mixture was evaporated and purified by preparative LCMS (pH 10) to give the desired compound (8.6 mg, 36%). LCMS calculated for C21H22ClN10O (M+H)+: m/z=465.2. found: 464.9.

Workup

  1. customThe mixture was evaporated
  2. customThe mixture was evaporated
  3. customThe mixture was evaporated
  4. custompurified by preparative LCMS (pH 10)

Sources & evidence

ORD record
ord-03cc0a00343a489c834b24ead9c9a103
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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