Diisopropylethylamine → HCID 178463582, compound

HRID 1192584Notes

Reaction equation

HRID 1192584 reaction equation
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[NH2:11][CH:12]([C:14]1[N:15]=[C:16]([C:31]#[N:32])[C:17]2[C:22]([C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)C>[F:30][C:26]1[CH:25]=[C:24]([C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([C:31]#[N:32])=[N:15][C:14]=2[CH:12]([NH:11][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH3:13])[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58368675HCID 58368675, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178463582HCID 178463582, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromo-9H-purine (5.48 mg, 0.0275 mmol), 3-(1-aminoethyl)-4-(3-fluorophenyl)isoquinoline-1-carbonitrile (4 mg, 0.01 mmol), and N,N-diisopropylethylamine (0.00480 mL, 0.0276 mmol) in ethanol (0.05 mL) was heated at 90° C. under nitrogen overnight. The mixture was evaporated and the resulting mixture 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. LCMS calculated for C23H17FN7 (M+H)+: m/z=410.2; Found: 410.1.

Workup

  1. customThe mixture was evaporated
  2. customthe resulting mixture was purified on a RP-HPLC (XBridge C18 column
  3. 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-c237b9275f6c4784989f5eb8d4952e87
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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