Lithium Hexamethyldisilazide → HCID 78162559, compound

HRID 1056180Notes

Reaction equation

HRID 1056180 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[NH:12][C:13]([C:20]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=2[N:22]=[C:23]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:24]([CH3:30])=[N:25]3)=[CH:14][C:15]=1[C:16]([O:18]C)=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>O1CCOCC1>[C:32]([NH:31][C:23]1[C:24]([CH3:30])=[N:25][C:26]2[C:21]([N:22]=1)=[C:20]([C:13]1[NH:12][C:11]3[CH:9]([CH3:10])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:16](=[O:18])[C:15]=3[CH:14]=1)[CH:29]=[CH:28][CH:27]=2)([CH3:34])([CH3:33])[CH3:35]

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 89784460HCID 89784460, compound

Product 1

HCID 78162559HCID 78162559, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (326b) (0.13 g, 0.27 mmol) in p-dioxane (2 mL) was added LiHMDS (1.64 mL, 1.64 mmol) dropwise. After the addition, the mixture was stirred at RT in overnight, then heated at 60° C. in 1 h, cooled to RT, and quenched with saturated aq. NH4Cl, extracted with EtOAc (3×). The extracts were dried over MgSO4, filtered, concentrated and purified by ISCO (0-70% EtOAc/Hexanes) to give the title compound (43 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.09 (1H, s), 7.78 (1H, dd, J=7.4, 1.4 Hz), 7.67 (1H, dd, J=8.2, 1.4 Hz), 7.38 (1H, t, J=7.7 Hz), 6.94 (1H, s), 6.00 (1H, s), 4.99 (1H, q, J=6.5 Hz), 2.56 (3H, s), 1.59 (3H, d, J=6.5 Hz), 1.52 (9H, s), 1.51 (9H, s). m/z (ESI, +ve) 450.0 (M+H)+.

Workup

  1. additionAfter the addition
  2. temperatureheated at 60° C. in 1 h
  3. temperaturecooled to RT
  4. customquenched with saturated aq. NH4Cl
  5. extractionextracted with EtOAc (3×)
  6. dry with materialThe extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by ISCO (0-70% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-8fd0228a875d49b19f40e543e371a02b
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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