Acetaldehyde → HCID 68909749, compound

HRID 729537Notes

Reaction equation

HRID 729537 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[CH:19]=2)[CH:9]=1.[CH:33](=O)[CH3:34].CO>C(Cl)(Cl)Cl.C(Cl)Cl>[CH2:33]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[CH:19]=2)[CH:9]=1)[CH3:34]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 887MethanolHCID 68908629HCID 68908629, compound

Product 1

HCID 68909749HCID 68909749, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 60 mg (0.14 mmol) {4-[4-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-quinolin-2-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine in 5 mL chloroform was treated with 0.1 mL (1.8 mmol) acetaldehyde, 113 mg (1.8 mmol) NaBH3(CN) and 1 mL methanol. The mixture was stirred at rt for 15 h. MS showed all starting materials were converted. The mixture was diluted with 100 mL DCM, washed with 20 mL sat. NaHCO3, and dried over anhydrous Na2SO4. After purification by chromatography, the title compound was obtained as a yellow solid. MS (ES+): 450 (M+H)+.

Workup

  1. washwashed with 20 mL sat. NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. customAfter purification by chromatography

Sources & evidence

ORD record
ord-a94fc89495904f44a7ee3987c908c66b
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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