1H-imidazole-2-carbaldehyde → HCID 58996998, compound

HRID 251182Notes

Reaction equation

HRID 251182 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[BH3-]C#N.[Na+].[NH:28]1[CH:32]=[CH:31][N:30]=[C:29]1[CH:33]=O>CO>[NH:28]1[CH:32]=[CH:31][N:30]=[C:29]1[CH2:33][N:13]1[CH2:14][CH2:15][CH:10]([N:9]([CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:8][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58996965Bis-(3-methyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine

Product 1

HCID 58996998HCID 58996998, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of COMPOUND 249 (0.1182 g, 0.38 mmol) in MeOH (8 mL) was added NaBH3CN (0.0477, 0.76 mmol) and 2-imidazole carboxaldehyde (0.0438 g, 0.46 mmol), and stirred at room temperature for 24 hours then concentrated. Saturated NaHCO3 (15 mL) was added and extracted with CH2Cl2 (2×40 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2-MeOH—NH4OH) provided 0.0486 g (31%) of COMPOUND 336 as a white solid. 1H NMR (CDCl3) δ 1.67-1.87 (m, 4H), 1.99 (t, 2H, J=11.3 Hz), 2.08 (s, 6H), 2.47-2.55 (m, 1H), 2.87 (d, 2H, J=11.1 Hz), 3.58 (s, 2H), 3.82 (s, 4H), 6.98 (s, 2H), 7.02-7.09 (m, 2H), 7.35 (d, 2H, J=7.2 Hz), 8.33 (d, 2H, J=3.9 Hz). 13C NMR (CDCl3) δ 18.39, 27.23, 54.15, 55.31, 56.25, 57.94, 121.88, 122.77, 127.09, 133.81, 138.42, 146.20, 157.67. ES-MS m/z 377 (M+Na+). Anal. Calcd. for C23H30N6.0.6CH4O: C, 69.18; H, 7.97; N, 20.51. Found: C, 69.05; H, 7.78; N, 20.39.

Workup

  1. concentrationthen concentrated
  2. additionSaturated NaHCO3 (15 mL) was added
  3. extractionextracted with CH2Cl2 (2×40 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record
ord-367404ea87b14f4eb88027a8574157a5
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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