Isoamylamine → HCID 86701564, compound

HRID 2173994Notes

Reaction equation

HRID 2173994 reaction equation
[CH3:1][C:2]1[C:3]([CH:22]([OH:34])[C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:25]=3[N:24]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7](S(C1C=CC(C)=CC=1)(=O)=O)[CH:6]=[CH:5]2.[OH-].[K+].C(N)CC(C)C>CCO>[CH3:1][C:2]1[C:3]([CH:22]([OH:34])[C:23]2[NH:24][C:25]3[CH:31]=[C:30]([C:32]#[N:33])[CH:29]=[CH:28][C:26]=3[N:27]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 14797Potassium HydroxideHCID 178427341HCID 178427341, compound

Product 1

HCID 86701564HCID 86701564, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (±)-2-((5,7-dimethyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile, KOH (84 mg, 1.50 mmol) and isoamylamine (0.35 mL, 3 mmol) in EtOH (1.5 mL) was heated at 100° C. for 1 h under the microwave irradiation. The reaction mixture was concentrated. The residue was diluted with CH2Cl2 and brine. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over NaSO3, filtered and evaporated. The resulting residue was purified by flash column chromatography on NH-modified silica gel (CH2Cl2:MeOH=100:0 to 10:1) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.90 (br.s, 1H) 10.84 (s, 1H) 7.87-7.91 (m, 1H) 7.56-7.61 (m, 1H) 7.45-7.50 (m, 1H) 7.14 (t, J=2.65 Hz, 1H) 6.71 (s, 1H) 6.44-6.45 (m, 1H) 6.35-6.36 (m, 1H) 2.43 (s, 3H) 2.39 (s, 3H). HRMS calcd. for C22H20N5O (M+H)+ 317.1397. found 317.1404.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was diluted with CH2Cl2 and brine
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. dry with materialThe combined organic extracts were dried over NaSO3
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting residue was purified by flash column chromatography on NH-modified silica gel (CH2Cl2:MeOH=100:0 to 10:1)

Sources & evidence

ORD record
ord-4e9962889f68449d815668106fc80aef
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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