Ethylenediamine → HCID 178489081, compound

HRID 2173938Notes

Reaction equation

HRID 2173938 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[C:6]([CH3:34])[CH:7]=[C:8]([O:32][CH3:33])[C:9]=2[CH:11]([OH:31])[C:12]2[N:16](COCC[Si](C)(C)C)[C:15]3[CH:25]=[CH:26][C:27]([C:29]#[N:30])=[CH:28][C:14]=3[N:13]=2)[NH:4][CH:3]=1.ClC1C2C(=C(C)C=C(OC)C=2C(O)C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)NC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(N)CN.[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[C:10]2[C:5](=[C:6]([CH3:34])[CH:7]=[C:8]([O:32][CH3:33])[C:9]=2[CH:11]([OH:31])[C:12]2[NH:16][C:15]3[CH:25]=[CH:26][C:27]([C:29]#[N:30])=[CH:28][C:14]=3[N:13]=2)[NH:4][CH:3]=1

Participants

8

Reactant 5

HCID 3301EthylenediamineHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 86701492HCID 86701492, compoundHCID 86701493HCID 86701493, compound

Product 1

HCID 178489081HCID 178489081, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (±)-2-((3-chloro-5-methoxy-7-methyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-((3-chloro-5-methoxy-7-methyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (0.2 g, 0.402 mmol) was dissolved in THF (4.02 mL) and treated with TBAF (1M in THF, 4.02 mL, 4.02 mmol) and ethylenediamine (0.272 mL, 4.02 mmol) and heated at 60° C. The reaction was cooled to room temperature, and treated with 10 mL of a saturated aq. solution of ammonium chloride and then diluted with EtOAc. The layers were separated and the organic layer was washed with water (3×100 mL). The organic extracts were combined, dried over magnesium sulfate, filtered and concentrated. The resulting residue was purified via FCC (0-100% EtOAc in heptanes) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.71 (d, J=6.57 Hz, 1H) 11.28 (br. s., 1H) 7.87 (d, J=6.19 Hz, 1H) 7.61 (m) 7.40-7.50 (m, 2H) 6.94-7.12 (m, 1H) 6.79 (s, 1H) 6.02-6.20 (m, 1H) 3.42-3.50 (m, 3H) 2.45 (s, 3H). HRMS calcd. for C19H16ClN4O2 (M+H)+ 367.0957. found 367.096.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with water (3×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified via FCC (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-ae71966aac6e439ab5ba2d13a6e37020
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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