Dimethyl Sulfoxide → HCID 88536553, compound

HRID 1774914Notes

Reaction equation

HRID 1774914 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Si:11]([O:18][C@@H:19]1[C@@H:24]([N:25]2[C:34](=[O:35])[C:33]3[C:28](=[C:29]4[CH:48]=[CH:47][CH:46]=[CH:45][C:30]4=[C:31]([CH2:36][C:37]4[CH:38]=[N:39][C:40]([CH2:43][OH:44])=[CH:41][CH:42]=4)[CH:32]=3)[N:27]=[CH:26]2)[CH2:23][CH2:22][O:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[Si:11]([O:18][C@@H:19]1[C@@H:24]([N:25]2[C:34](=[O:35])[C:33]3[C:28](=[C:29]4[CH:48]=[CH:47][CH:46]=[CH:45][C:30]4=[C:31]([CH2:36][C:37]4[CH:42]=[CH:41][C:40]([CH:43]=[O:44])=[N:39][CH:38]=4)[CH:32]=3)[N:27]=[CH:26]2)[CH2:23][CH2:22][O:21][CH2:20]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:12])[CH3:13]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 679698743-((3R,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-4-yl)-6-{[6-(hydroxymethyl)pyridine-3-yl]methyl}benzo[h]quinazolin-4(3H)-one

Product 1

HCID 88536553HCID 88536553, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dimethylsulfoxide (0.040 mL, 0.56 mmol) in 2 mL of dichloromethane at −78° C. was added oxalyl chloride (0.025 mL, 0.28 mmol). After 30 min, a solution of 3-((3R,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-4-yl)-6-{[6-(hydroxymethyl)pyridine-3-yl]methyl}benzo[h]quinazolin-4(3H)-one (Example 21, 0.075 g, 0.14 mmol) in 1 mL of dichloromethane. After 30 min, triethylamine (0.157 mL, 1.13 mmol) was added, and the reaction was warmed to rt. After 30 min, the mixture was treated with saturated aqueous ammonium chloride and extracted 2× with diethyl ether. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 5-{[3-((3R,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-4-yl)-4-oxo-3,4-dihydrobenzo[h]quinazolin-6-yl]methyl}pyridine-2-carbaldehyde that gave proton NMR spectra consistent with theory.

Workup

  1. waitAfter 30 min
  2. waitAfter 30 min
  3. extractionextracted 2× with diethyl ether
  4. dry with materialThe combined organic fractions were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2378d75984e24c9c88f8ed449f65f6eb
Source dataset
uspto-grants-2016_02
Patent number
US09260418B2

Reaction notes

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