Diisopropylethylamine → HCID 178422556, compound

HRID 243288Notes

Reaction equation

HRID 243288 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]([C@@H:9]([NH2:11])[CH3:10])=[N:8][C:4]=2[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[CH:19]=[CH:18][C:5]2[N:6]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:7]([C@@H:9]([NH:11][C:21]3[N:29]=[CH:28][N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][NH:25]4)[CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 68157346HCID 68157346, compoundHCID 178478393HCID 178478393, compound

Product 1

HCID 178422556HCID 178422556, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (S)-1-(5-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine from Example 14 (100 mg, 0.398 mmol), 6-chloro-9H-purine (74 mg, 0.478 mmol) and DIPEA (0.347 mL, 1.99 mmol) in n-butanol (2 mL) was stirred in a sealed vial for 20 h at 120° 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 triturated with acetonitrile affording 117 as an off-white solid (54 mg, 37%). LCMS: RT 3.11 min [M+H]+ 370.1. 1H NMR (DMSO, 400 MHz): δ 12.90 (1H, bs), 8.20-8.00 (2H, m), 7.84 (1H, s), 7.69-7.39 (6H, m), 7.07-6.89 (2H, m), 5.49 (1H, bs), 2.39 (3H, s), 1.53 (3H, d, J=6.79 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. customtriturated with acetonitrile affording 117 as an off-white solid (54 mg, 37%)

Sources & evidence

ORD record
ord-e321951c663a40679cf9170d1fb97b88
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…