Sodium triacetoxyborohydride → HCID 69311958, compound

HRID 33231Notes

Reaction equation

HRID 33231 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)=[N:5][N:4]=[C:3]1[S:17][CH2:18][CH2:19][CH2:20][CH:21]=O.[CH2:23]([S:25]([C:28]1[CH:38]=[CH:37][C:31]2[CH2:32][CH2:33][NH:34][CH2:35][CH2:36][C:30]=2[CH:29]=1)(=[O:27])=[O:26])[CH3:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:23]([S:25]([C:28]1[CH:38]=[CH:37][C:31]2[CH2:32][CH2:33][N:34]([CH2:21][CH2:20][CH2:19][CH2:18][S:17][C:3]3[N:2]([CH3:1])[C:6]([C:7]4[CH:8]=[C:9]5[C:14](=[CH:15][CH:16]=4)[N:13]=[CH:12][CH:11]=[CH:10]5)=[N:5][N:4]=3)[CH2:35][CH2:36][C:30]=2[CH:29]=1)(=[O:26])=[O:27])[CH3:24]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 69181179HCID 69181179, compoundHCID 865941734-(4-Methyl-5-quinolin-6-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-butyraldehyde

Product 1

HCID 69311958HCID 69311958, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(4-Methyl-5-quinolin-6-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-butyraldehyde (0.1 g, 0.32 mmol) and 7-Ethanesulfonyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.11 g, 0.45 mmol) were stirred at room temperature in dichloromethane (4 ml) for 20 min. Sodium triacetoxyborohydride (71 mg, 0.34 mmol) was then added and the mixture stirred overnight. The mixture was diluted with dichloromethane (50 ml) and washed with saturated sodium bicarbonate solution (30 ml). The aqueous was extracted with further dichloromethane (50 ml) and the combined organic portions were dried (Na2SO4), filtered and evaporated to give a yellow oil. Purification by silica gel chromatography (eluent 10% MeOH:EtOAc) which gave the title compound as a colourless oil (35 mg, 21%).

Workup

  1. washwashed with saturated sodium bicarbonate solution (30 ml)
  2. extractionThe aqueous was extracted with further dichloromethane (50 ml)
  3. dry with materialthe combined organic portions were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a yellow oil
  7. customPurification by silica gel chromatography (eluent 10% MeOH:EtOAc) which

Sources & evidence

ORD record
ord-f6b7a8833b22409d8684a62ec3804fae
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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