Water → HCID 67763710, compound

HRID 362927Notes

Reaction equation

HRID 362927 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:26])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:17])[CH2:3][CH2:2]1.[BH3-]C#N.[Na+].[CH:31]([C:34]1[C:39]([CH:40]=O)=[C:38]([C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=2)[C:37]([CH2:49][O:50][CH3:51])=[C:36]([CH:52]([CH3:54])[CH3:53])[N:35]=1)([CH3:33])[CH3:32].O>CO>[CH:31]([C:34]1[C:39]([CH2:40][N:1]2[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:26])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:17])[CH2:3][CH2:2]2)=[C:38]([C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=2)[C:37]([CH2:49][O:50][CH3:51])=[C:36]([CH:52]([CH3:54])[CH3:53])[N:35]=1)([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 101720502,6-Diisopropyl-4-(4-fluorophenyl)-5-methoxymethylpyridine-3-carboxaldehydeHCID 53783949HCID 53783949, compound

Product 1

HCID 67763710HCID 67763710, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step 2): N-(Piperidin-4-yl)-2-(N'-n-heptylureido)benzamide (0.96 g, 2.7 mmol) and NaBH3CN (0.17 g, 2.7 mmol) were added into a solution of 2.6-diisopropyl-4-(4-fluorophenyl)-3-formyl-5-methoxymethylpyridine (0.9 g, 2.7 mmol) in MeOH (30 ml). The mixture was stirred at room temperature for 72 hours, and then water was added at 0° C. extracted with dichloromethane, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (10 to 50% ethyl acetate in hexane) to give N-[1-[2,6-diisopropyl-4-(4-fluorophenyl)-5-(methoxymethyl)pyridin-3-yl]methylpiperidin-4-yl]-2-(N'-n-heptylureido)benzamide (0.65 g, 35.7%): mp 123° C.: 1NMR (CDCl3)ppm: 0.88 (3H, t), 1.17-1.46 (22H, m), 1.49-1.66 (2H, m), 1.80-2.00 (4H, m), 2.57 (2H, d), 3.09-3.53 (9H, m), 3.68-3.89 (1H, m), 3.49 (2H, s), 4.53 (1H, t), 5.98 (1H, d), 6.93 (1H, t), 7.05-7.24 (4H, m), 7.33-7.48 (2H, m), 8.41 (1H, d), 10.30 (1H, s).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (10 to 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-882da23ae74b4a9d8f5d1ae1b885ef7b
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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