Borohydride → HCID 58828971, compound

HRID 1171450Notes

Reaction equation

HRID 1171450 reaction equation
[BH4-].[CH2:2]([C:9]1[N:10]([CH3:15])[C:11]([SH:14])=[N:12][N:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].I[C:17]1[CH:36]=[CH:35][C:20]([CH2:21][NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:25][CH:24]=2)=[C:19]([O:37][CH2:38][CH2:39][CH3:40])[CH:18]=1>O1CCCC1.C(O)C>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][CH2:21][C:20]2[CH:35]=[CH:36][C:17]([S:14][C:11]3[N:10]([CH3:15])[C:9]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[N:13][N:12]=3)=[CH:18][C:19]=2[O:37][CH2:38][CH2:39][CH3:40])=[CH:24][CH:25]=1)[CH3:34]

Participants

5

Reactant 3

HCID 28123BorohydrideHCID 58828974HCID 58828974, compoundHCID 178442555HCID 178442555, compound

Product 1

HCID 58828971HCID 58828971, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent2×

Procedure

2.647 g (6.62 mmol, 3 eq) of resin-supported borohydride and 30 mg (0.06 mmol, 0.03 eq) of bis(bipyridine)dibromonickel (II) are added to a solution of 0.706 g (3.31 mmol, 1.5 eq) of 5-heptyl-4-methyl-4H-[1,2,4]-triazole-3-thiol in 10 ml of tetrahydrofuran/ethanol 5/5. To the suspension obtained there is added a solution of 100 mg (0.22 mmol, 1 eq) of ethyl [4-(4-iodo-2-propoxybenzylamino)phenyl]acetate in 10 ml of tetrahydrofuran/ethanol 5/5. The reaction mixture is stirred overnight under reflux. After returning to room temperature, the reaction medium is filtered, concentrated and then chromatographed on silica gel (heptane/ethyl acetate 40/60). After evaporation of the solvents, 0.750 g (63%) of the expected compound is recovered.

Workup

  1. customTo the suspension obtained there
  2. temperatureunder reflux
  3. customAfter returning to room temperature
  4. filtrationthe reaction medium is filtered
  5. concentrationconcentrated
  6. customchromatographed on silica gel (heptane/ethyl acetate 40/60)
  7. customAfter evaporation of the solvents, 0.750 g (63%) of the expected compound
  8. customis recovered

Sources & evidence

ORD record
ord-451756e1e3eb4ffaa47f27b4a5a7d69c
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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