Acetic Acid → HCID 131722157, compound

HRID 1858109Notes

Reaction equation

HRID 1858109 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH2:23][C@@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]3)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[NH:30][C:31]([C:33]1[CH:38]=[CH:37][N:36]=[CH:35][N:34]=1)=[O:32].C=O.[C:41](O)(=O)C.C([BH3-])#N.[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH2:23][C@@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][N:25]3[CH3:41])=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[NH:30][C:31]([C:33]1[CH:38]=[CH:37][N:36]=[CH:35][N:34]=1)=[O:32]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 54147199HCID 54147199, compound

Product 1

HCID 131722157HCID 131722157, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pyrimidine-4-carboxylic acid (S)-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-amide (prepared essentially as described in EXAMPLE 2, 9 mg in 0.40 mL methanol) was added 6 mg paraformaldehyde followed by 20 mg powdered 4A molecular sieves and 0.01 mL acetic acid and the mixture stirred at room temperature for 10 minutes. At this time, 5 mg sodium cyanoborohydride was added and the stirring continued. After 2 hours, 0.5 mL tetrahydrofuran was added to ensure homogeneity and after 60 hours the reaction was quenched by the addition of water. The reaction mixture was extracted with methylene chloride and the combined organics washed with brine and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:10% ammonium hydroxide in methanol, 95:5; then 92:8) gave the title compound (6.7 mg). MASS: 546 (M+H) ##STR167##

Workup

  1. waitAfter 2 hours
  2. customafter 60 hours the reaction was quenched by the addition of water
  3. extractionThe reaction mixture was extracted with methylene chloride
  4. washthe combined organics washed with brine
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-5ac62cc6e5a64af09f6b6dea4cf25e77
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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