Borohydride → Ethyl(4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)acetate

HRID 1171434Notes

Reaction equation

HRID 1171434 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[C:27](I)[CH:26]=[CH:25][C:10]=1[CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:30]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[N:41]([CH3:46])[C:42]([SH:45])=[N:43][N:44]=2)=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31].[BH4-]>O1CCCC1.C(O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][CH2:11][C:10]2[CH:25]=[CH:26][C:27]([S:45][C:42]3[N:41]([CH3:46])[C:40]([C:37]4[CH:38]=[CH:39][C:34]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:35][CH:36]=4)=[N:44][N:43]=3)=[CH:28][C:9]=2[O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:14][CH:15]=1)[CH3:24]

Participants

6

Reactant 3

HCID 28123BorohydrideHCID 86611168Ethyl [4-(2-heptyloxy-4-iodobenzylamino)phenyl]acetateHCID 178481686HCID 178481686, compound

Product 1

HCID 11227433Ethyl(4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)acetate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl [4-(2-heptyloxy-4-iodo benzylamino)phenyl]acetate obtained in Step d (4.11 g, 8.07 mmol) in a mixture of tetrahydrofuran (THF) (18 ml) and ethanol (18 ml) is added dropwise to a mixture of 5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazole-3-thiol (2.99 g, 12.1 mmol), bis(bipyridine)nickel (II) bromide (106 mg, 0.2 mmol) (Organometallics, 4, (1985), 657-661) and 9.68 g of borohydride polymer supported on Amberlite® IRA400 resin at 2.5 mmol/g (Aldrich) in 18 ml of a mixture of THF and ethanol 50:50. The mixture is heated for 20 hours under reflux, and then filtered at room temperature. The filtrate is concentrated using a rotary evaporator. The product is purified by chromatography on a silica column, eluted with a heptane/ethyl acetate 7:3 mixture. After evaporation of the solvents, 4.58 g (90%) of the expected compound are recovered in the form of an oil.

Workup

  1. temperatureThe mixture is heated for 20 hours
  2. temperatureunder reflux
  3. filtrationfiltered at room temperature
  4. concentrationThe filtrate is concentrated
  5. customa rotary evaporator
  6. customThe product is purified by chromatography on a silica column
  7. washeluted with a heptane/ethyl acetate 7:3 mixture
  8. customAfter evaporation of the solvents, 4.58 g (90%) of the expected compound
  9. customare recovered in the form of an oil

Sources & evidence

ORD record
ord-fe966cb0b4b5497d85742391141660b8
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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