Diisopropylethylamine → HCID 178461875, compound

HRID 243420Notes

Reaction equation

HRID 243420 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH2:12])[CH3:11])[N:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.Cl[C:21]1[N:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][NH:25]2.CCN(C(C)C)C(C)C>CC(O)C>[NH3:7].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:12][C:21]3[N:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][NH:25]4)[CH3:11])[N:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 68157234(S)-1-(6-Fluoro-1-pyrid-2-yl-1H-benzoimidazol-2-yl)ethylamineHCID 178506275HCID 178506275, compound

Product 2

HCID 222AmmoniaHCID 178461875HCID 178461875, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethylamine (0.055 g, 0.22 mmol), 6-chloro-2-trifluoromethyl-9H-purine (0.040 g, 0.18 mmol) and DIPEA (0.096 mL, 5.39 mol) in IPA (1 mL) was stirred at 80° C. in a sealed tube for 16 h. The resulting mixture was concentrated in vacuo and the residue purified by chromatography (SiO2, O-15% (2M ammonia in methanol) in DCM) then by preparative HPLC (Phenomenex Gemini 5 μm C18 on a 60 min gradient 20-98% 0.1% HCO2H in acetonitrile/water) to give 313 as a white solid (0.042 g, 23%). LCMS (method K): Rt 4.11 min, [M+H]+ 443. 1H NMR (DMSO-d6) δ: 13.20-12.70 (1H, bs), 8.59 (2H, m), 8.32 (1H, s), 7.97 (1H, m), 7.74-7.67 (2H, m), 7.43 (1H, s), 7.16-7.13 (2H, m), 5.86 (1H, m), 1.69 (3H, d, J=6.82 Hz)

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe residue purified by chromatography (SiO2

Sources & evidence

ORD record
ord-ba0a32b6854d40139a2e7ef6b20b1c45
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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