Benzaldehyde → HCID 178522223, compound

HRID 1630297Notes

Reaction equation

HRID 1630297 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)=[O:16])=[O:8])[N:3]=[CH:2]1.[CH:32](=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:11][C@H:10]2[C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:22][CH:23]=2)=[O:16])=[O:8])[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 178522224HCID 178522224, compound

Product 1

HCID 178522223HCID 178522223, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step (b) A flask was charged with (S)-1-(2-(1H-imidazol-4-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)piperazine-2-carboxamide (107 mg, 0.252 mmol), benzaldehyde (0.154 mL, 1.51 mmol), methanol (10 mL) and sodium triacetoxyborohydride (534 mg, 2.52 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes and then diluted with deionized water (15 mL). The mixture was washed with ethylene chloride (20 mL) and the aqueous layer was basified with 2N sodium hydroxide (40 mL) and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give Compound 175 (S)-1-(2-(1H-imidazol-4-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)piperazine-2-carboxamide (41 mg, 32% yield), as an off-white solid. 1H-NMR (400 MHz, CDCl3): 10.23 (s, 1H), 7.63-7.18 (m, 8H), 7.02-6.82 (m, 7H), 5.42 (s, 1H), 4.02-3.90 (m, 1H), 3.88-3.80 (m, 1H), 3.78-3.61 (m, 2H), 3.58-3.34 (m, 2H), 3.08-2.97 (m, 1H), 2.78-2.64 (m 1H), 2.28-2.18 (m, 1H), 2.11-2.00 (m, 1H). MS (EI) for C29H28FN5O3. found 514.3 (MH+).

Workup

  1. washThe mixture was washed with ethylene chloride (20 mL)
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f12f488f649487386ff24198a91c3da
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…