Water → HCID 59493242, compound

HRID 1893176Notes

Reaction equation

HRID 1893176 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[C:5]([CH3:34])([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:17]=[C:16]([NH2:26])[N:15]=2)=[CH:9][CH:8]=1)[CH3:2].[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH:42]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl>[CH2:1]([O:3][C:4](=[O:35])[C:5]([CH3:34])([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([N:20]3[CH2:21][CH2:22][N:23]([CH2:42][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][N:36]=4)[CH2:24][CH2:25]3)[N:17]=[C:16]([NH2:26])[N:15]=2)=[CH:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59493240HCID 59493240, compound

Product 1

HCID 59493242HCID 59493242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 3-[4-(2-Amino-6-piperazin-1-yl-pyrimidin-4-yloxy)-phenyl]-2-methyl-2-phenoxy-propionic acid ethyl ester (1 mmol) in dry dichloromethane (20 ml) under N2 was added pyridine-2-carbaldehyde (1.1 mmol). The reaction was stirred at room temperature for half an hour, then Sodium triacetoxyborohydride (1.3 mmol) was then added and stirred over night. Water (10 mL), the biphasic mixture was diluted with dichloromethane and partitioned, and the organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified in silica to provide yellow solid.

Workup

  1. stirringstirred over night
  2. custompartitioned
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified in silica
  7. customto provide yellow solid

Sources & evidence

ORD record
ord-f0f23d13264c49df9f845f5700ea4369
Source dataset
uspto-grants-2013_08
Patent number
US08513233B2

Reaction notes

Loading…