Sodium triacetoxyborohydride → 7-(5-Methyl-isoxazol-3-yl)-3-{4-[4-methyl-5-(2-methyl-quinolin-6-yl)-4 H-[1,2,4]triazol-3-yl]-butyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 33228Notes

Reaction equation

HRID 33228 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]=[C:12]([CH3:17])[CH:11]=[CH:10]3)=[N:5][N:4]=[C:3]1[CH2:18][CH2:19][CH2:20][CH:21]=O.[CH3:23][C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:39]=[CH:38][C:32]3[CH2:33][CH2:34][NH:35][CH2:36][CH2:37][C:31]=3[CH:30]=2)[CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:23][C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:39]=[CH:38][C:32]3[CH2:33][CH2:34][N:35]([CH2:21][CH2:20][CH2:19][CH2:18][C:3]4[N:2]([CH3:1])[C:6]([C:7]5[CH:8]=[C:9]6[C:14](=[CH:15][CH:16]=5)[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10]6)=[N:5][N:4]=4)[CH2:36][CH2:37][C:31]=3[CH:30]=2)[CH:25]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 690161167-(5-Methyl-isoxazol-3-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 865941724-[4-Methyl-5-(2-methyl-quinolin-6-yl)-4H-[1,2,4]triazol-3-yl]-butyraldehyde

Product 1

HCID 99360047-(5-Methyl-isoxazol-3-yl)-3-{4-[4-methyl-5-(2-methyl-quinolin-6-yl)-4 H-[1,2,4]triazol-3-yl]-butyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 21.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[4-Methyl-5-(2-methyl-quinolin-6-yl)-4H-[1,2,4]triazol-3-yl]-butyraldehyde (76 mg, 0.25 mmol) and 7-(5-Methyl-isoxazol-3-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (55 mg, 0.24 mmol) were stirred at room temperature in dichloromethane (5 ml) for 30 min. Sodium triacetoxyborohydride (55 mg, 0.26 mmol) was then added and the mixture stirred over the weekend. 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 the desired compound as an off-white solid (26 mg).

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

Sources & evidence

ORD record
ord-dc4cb302b3ec43bfa74120ce7103a772
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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