Diisopropylethylamine → HCID 178456064, compound

HRID 243290Notes

Reaction equation

HRID 243290 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:16]([NH2:19])[CH2:17][CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][NH:25]2.CCN(C(C)C)C(C)C>O1CCOCC1>[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:16]([NH:19][C:21]2[N:29]=[CH:28][N:27]=[C:26]3[C:22]=2[N:23]=[CH:24][NH:25]3)[CH2:17][CH3:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 68157690(S)-1-(1-Phenyl-1H-benzoimidazol-2-yl)propylamineHCID 178478393HCID 178478393, compound

Product 1

HCID 178456064HCID 178456064, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (S)-1-(1-phenyl-1H-benzoimidazol-2-yl)propylamine from Example 12 (100 mg, 0.398 mmol), 6-chloro-9H-purine (65 mg, 0.418 mmol) and DIPEA (0.348 mL, 2.0 mmol) in dioxane (3 mL) was stirred for 24 h at 100° C. After cooling to RT, volatiles were removed under reduced pressure and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% MeOH in EtOAc) and then crystallised from acetonitrile affording 119 as a white solid (50 mg, 34%). LCMS: RT 3.23 min [M+H]+ 370.0. 1H NMR (DMSO, 400 MHz): δ 8.21-8.07 (2H, m), 7.86-7.49 (7H, m), 7.28-7.17 (2H, m), 7.08 (1H, d, J=7.68 Hz), 5.42 (1H, br), 2.08-1.90 (2H, m), 0.83 (3H, t, J=7.32 Hz)

Workup

  1. temperatureAfter cooling to RT
  2. customvolatiles were removed under reduced pressure
  3. customthe resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% MeOH in EtOAc)
  4. customcrystallised from acetonitrile affording 119 as a white solid (50 mg, 34%)

Sources & evidence

ORD record
ord-835d184c4be444cf9b803902285f47bb
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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