Diisopropylethylamine → HCID 178423968, compound

HRID 243281Notes

Reaction equation

HRID 243281 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]([C@@H:11]([NH2:13])[CH3:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=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>C(O)CCC>[CH3:1][C:2]1[C:7]2[N:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]([C@@H:11]([NH:13][C:21]3[N:29]=[CH:28][N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][NH:25]4)[CH3:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 68157399(S)-1-(7-Methyl-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamineHCID 178478393HCID 178478393, compound

Product 1

HCID 178423968HCID 178423968, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (S)-1-(7-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine from Example 1 (100 mg, 0.398 mmol), 6-chloro-9H-purine (65 mg, 0.418 mmol) and DIPEA (77 μL, 0.438 mmol) in n-butanol (2 mL) was stirred at 140° C. for 1 h under microwave irradiation. Volatiles were removed under reduced pressure and the residue was partitioned between DCM and water. The organic phase was then separated, dried and concentrated in vacuo. The resulting crude material was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) and then triturated with IMS affording 110 as a white solid (6.2 mg, 4%) LCMS: RT 3.08 min [M+H]+ 370.1. 1H NMR (DMSO, 400 MHz): δ 8.12 (1H, bs), 8.07 (1H, s), 7.83-7.75 (1H, m), 7.64-7.37 (7H, m), 7.09 (1H, t, J=7.67 Hz), 6.92 (1H, d, J=7.29 Hz), 5.25 (1H, br), 1.81 (3H, s), 1.54 (3H, d, J=6.84 Hz)

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe residue was partitioned between DCM and water
  3. customThe organic phase was then separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude material was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)
  7. customtriturated with IMS affording 110 as a white solid (6.2 mg, 4%) LCMS: RT 3.08 min [M+H]+ 370.1

Sources & evidence

ORD record
ord-d4f452a45985471b9e2e26e9c5c075bd
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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