Diisopropylethylamine → HCID 178432318, compound

HRID 243333Notes

Reaction equation

HRID 243333 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]([NH2:18])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:20]1[N:28]=[CH:27][N:26]=[C:25]2[C:21]=1[N:22]=[C:23]([CH3:29])[NH:24]2.C(N(C(C)C)C(C)C)C>C(O)CCC>[CH3:29][C:23]1[NH:24][C:25]2[C:21]([N:22]=1)=[C:20]([NH:18][C@H:16]([C:8]1[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=1)[CH3:17])[N:28]=[CH:27][N:26]=2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 68157455(S)-1-(1-Phenyl-1H-benzo[D]imidazol-2-YL)ethanamineHCID 1784322486-chloro-8-methyl-1H-purine

Product 1

HCID 178432318HCID 178432318, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (1S)-1-(1-phenyl-1H-1,3-benzodiazol-2-yl)ethan-1-amine from Example 4 (150 mg, 0.62 mmol, 1.00 equiv, 98%), 6-chloro-8-methyl-9H-purine (150 mg, 0.87 mmol, 1.41 equiv) and ethylbis(propan-2-yl)amine (0.3 mL, 98%) in butan-1-ol (6 mL) was stirred overnight at 130° C. The resulting mixture was concentrated under vacuum. The residue was purified on a C18 column eluted with water/acetonitrile to give 75 mg (30%) of 158 as a white solid. LC-MS (ES, m/z) 370 [M+H]+. H-NMR (300 MHz CD3OD, ppm) δ 8.04 (s, 1H), 7.69 (d, 1H), 7.55 (m, 5H), 7.30 (m, 2H), 7.11 (d, 1H), 5.63 (s, 1H), 2.55 (s, 3H), 1.71 (d, 3H)

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customThe residue was purified on a C18 column
  3. washeluted with water/acetonitrile

Sources & evidence

ORD record
ord-82ed1481e29342949b9de79c2ceef3ed
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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