Isobutyraldehyde → HCID 11541876, compound

HRID 1432026Notes

Reaction equation

HRID 1432026 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]2[N:21]=[N:22][N:23]([C@H:25]3[C:38]4[CH:37]=[CH:36][C:35]5[CH2:34][NH:33][CH2:32][CH2:31][C:30]=5[C:29]=4[CH2:28][CH2:27][CH2:26]3)[CH:24]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:39](=O)[CH:40]([CH3:42])[CH3:41].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]2[N:21]=[N:22][N:23]([C@H:25]3[C:38]4[CH:37]=[CH:36][C:35]5[CH2:34][N:33]([CH2:39][CH:40]([CH3:42])[CH3:41])[CH2:32][CH2:31][C:30]=5[C:29]=4[CH2:28][CH2:27][CH2:26]3)[CH:24]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11556017HCID 11556017, compound

Product 1

HCID 11541876HCID 11541876, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ((R)-4-(3,4-dichlorophenylsulfonyl)-3-((1-((R)-1,2,3,4,7,8,9,10-octahydrobenzo[f]isoquinolin-7-yl)-1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydropyrazin-2(1H)-one (220 mg, 0.384 mmol) and isobutyraldehyde (83 mg, 1.15 mmol) in 3 mL of 1,2-dichloroethane was added sodium triacetoxyborohydride (163 mg, 0.768 mmol) and the resulting solution was stirred at RT overnight. The reaction mixture was quenched with sat. NaHCO3, extracted with EtOAc, dried over Na2SO4, filtered and evaporated to dryness. Flash chromatography (SiO2, EtOAc to EtOAc/MeOH=100:7 to 100:12 to 100:14) afforded the title compound as a white solid.

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-0e37716f11ce44fcb1658a3add480d8d
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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