Diethyl Ether → HCID 15952275, compound

HRID 2244251Notes

Reaction equation

HRID 2244251 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31]([NH:33][CH2:34][C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:11][CH:10]=1)=[O:2].C[Mg]Br.[CH2:44](OCC)[CH3:45]>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31]([NH:33][CH2:34][C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:13][CH:14]=1)[CH2:44][CH3:45]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 15952274HCID 15952274, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 15952275HCID 15952275, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10-[(2′-formyl-1,1′-biphenyl-4-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 56 (0.132 g, 0.251 mmol) in dry tetrahydrofuran (15 mL) was added 3.0 Methylmagnesium bromide in diethyl ether (0.68 mL, 2.04 mmol) and the reaction mixture stirred at room temperature under nitrogen for 17 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (20 mL) and then the mixture partitioned between ethyl acetate (100 mL) and half saturated aqueous ammonium chloride solution (100 mL). The organic phase was separated, washed with brine (100 ml), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a cream foam. Purification by flash chromatography using a solvent gradient of 1 to 6% methanol in dichloromethane gave a colorless glass that was triturated with diethyl ether to afford the title compound (0.039 g, 28%) as a white solid, m.p. 111-115° C.

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride solution (20 mL)
  2. customthe mixture partitioned between ethyl acetate (100 mL) and half saturated aqueous ammonium chloride solution (100 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford a cream foam
  8. customPurification by flash chromatography
  9. customgave a colorless glass that
  10. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-520f7fa2583b4519b533cadc6bdd4d02
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

Loading…