Acetic Acid → HCID 68781049, compound

HRID 2264414Notes

Reaction equation

HRID 2264414 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([NH:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:7][CH:8]=1)[CH3:2].[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH:22]=O)[CH3:17].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:22][N:13]1[CH2:14][CH2:15][CH:10]([NH:9][C:6]2[N:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=2)[CH2:11][CH2:12]1)[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2447283-Ethoxy-4-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58972434HCID 58972434, compound2×

Product 1

HCID 68781049HCID 68781049, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
55 °C

Procedure

To a solution of (5-ethyl-pyrimidin-2-yl)-piperidin-4-yl-amine (30.9 mg, 0.15 mmol, 1.0 equiv; intermediate C1) and 3-ethoxy-4-methoxy-benzaldehyde (32.4 mg, 0.18 mmol, 1.2 equiv; commercially available) in ethanol (2 mL) was added acetic acid (27.0 mg, 0.45 mmol, 3.0 equiv) and the mixture stirred at 55° C. After 1 h sodium cyano borohydride (47.1 mg, 0.75 mmol, 5.0 equiv), dissolved in ethanol (0.5 mL), was added and the mixture stirred at 55° C. over night. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 21.0 mg (38%) of the title compound. MS (ESI): 371.5 [M+H]+.

Workup

  1. additionwas added
  2. stirringthe mixture stirred at 55° C. over night
  3. customRemoval of the solvent
  4. customunder reduced pressure and purification by preparative HPLC on reversed phase
  5. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-9042697fb3b5417d9e0a996e0337f0eb
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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