Dichloromethane → HCID 86646719, compound

HRID 1809112Notes

Reaction equation

HRID 1809112 reaction equation
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[CH3:24][N:25]1[CH:29]=[C:28]([CH:30]=O)[CH:27]=[N:26]1.[C:32]([O:35][BH-](OC(=O)C)OC(=O)C)(=[O:34])C.[Na+].C(Cl)Cl>ClCCCl>[CH:32]([O-:35])=[O:34].[CH3:24][N:25]1[CH:29]=[C:28]([CH2:30][N@H+:21]2[CH2:20][CH2:19][C@@H:18]([C:16]3[S:15][CH:14]=[C:13]([C:11]([N:1]4[CH:10]5[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]5)[CH2:4][CH2:3][CH2:2]4)=[O:12])[CH:17]=3)[CH2:23][CH2:22]2)[CH:27]=[N:26]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 86646702cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone

Product 1

HCID 86646719HCID 86646719, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.072 g, 0.21 mmol) and 1-methyl-1H-pyrazole-4-carboxaldehyde (0.33 mmol) were dissolved in DCE (3 mL). Sodium triacetoxyborohydride (0.33 mmol) was added and the mixture stirred for 6 hours. A second portion of sodium triacetoxyborohydride was added and the mixture stirred for 72 hours. DCM (25 mL) was added and the organic solution was washed with saturated sodium carbonate solution then brine, and then dried with anhydrous magnesium sulphate. The solvent was removed under vacuum and the resulting gum purified by HPLC eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (0.047 g). LCMS m/z 427.31 [M+H]+ RT=6.70 min (Analytical Method 2).

Workup

  1. stirringthe mixture stirred for 72 hours
  2. washthe organic solution was washed with saturated sodium carbonate solution
  3. dry with materialbrine, and then dried with anhydrous magnesium sulphate
  4. customThe solvent was removed under vacuum
  5. customthe resulting gum purified by HPLC
  6. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-b483477930264843802463bdbdff68eb
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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