Acetaldehyde → HCID 66763373, compound

HRID 578671Notes

Reaction equation

HRID 578671 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH:5]([NH:12][C:13]1[C:22]2[C:17](=C(C(N)=O)[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC[N:28](CC)CC.[CH:33](=[O:35])[CH3:34].[BH-](O[C:46]([CH3:48])=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.CCO>[CH2:46]([N:3]([CH3:2])[CH2:4][CH:5]([NH:12][C:13]1[C:22]2[C:17](=[C:34]([C:33]([NH2:28])=[O:35])[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH3:48]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 66763412HCID 66763412, compound

Product 1

HCID 66763373HCID 66763373, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

A 20 mL scintillation vial equipped with a stir bar was charged with 4-(2-methylamino-1-phenyl-ethylamino)-quinazoline-8-carboxylic acid amide hydrochloride salt, (32 mg, 0.1 mmol), EtOH, (5 mL) and Et3N, (0.03 mL, 0.2 mmol). The mixture was stirred until the amine had dissolved. Then AcOH (10 drops) was added followed by acetaldehyde, (0.1 mL, 2.0 mmol) and then NaBH(OAc)3, (212 mg, 1.0 mmol). The mixture was stirred at RT. After 30 minutes, the reaction was quenched by addition of 1N NaOH, (20 mL) diluted with EtOAc (25 mL) and the phases were split. The aqueous was extracted with EtOAc, (25 mL) (×2), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The material was purified by chromatography eluting with DCM-[DCM-MeOH—NH4OH (9:1:0.1)] Amount obtained: 15 mg, 40% yield. LCMS (ESI) 350 (M+H).

Workup

  1. customA 20 mL scintillation vial equipped with a stir bar
  2. dissolutionhad dissolved
  3. customthe reaction was quenched by addition of 1N NaOH, (20 mL)
  4. additiondiluted with EtOAc (25 mL)
  5. customthe phases were split
  6. extractionThe aqueous was extracted with EtOAc, (25 mL) (×2)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe material was purified by chromatography
  10. washeluting with DCM-[DCM-MeOH—NH4OH (9:1:0.1)] Amount
  11. customobtained

Sources & evidence

ORD record
ord-368edada1193498083badd6bd3b60a63
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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