1-Methyl-1H-pyrazole-4-carbaldehyde → HCID 57305885, compound

HRID 1375004Notes

Reaction equation

HRID 1375004 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]([F:51])([F:50])[C:17]1[CH:18]=[C:19]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][C@H:23]1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([O:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=1)=[O:21].[CH3:52][N:53]1[CH:57]=[C:56]([CH:58]=O)[CH:55]=[N:54]1>ClCCl>[F:51][C:16]([F:15])([F:50])[C:17]1[CH:18]=[C:19]([CH:43]=[C:44]([C:46]([F:47])([F:48])[F:49])[CH:45]=1)[C:20]([N:22]1[CH2:27][CH2:26][N:25]([CH2:58][C:56]2[CH:55]=[N:54][N:53]([CH3:52])[CH:57]=2)[CH2:24][C@H:23]1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([O:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=1)=[O:21]

Participants

5

Reactant 3

HCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 53740990HCID 53740990, compound

Product 1

HCID 57305885HCID 57305885, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.3 g) was added in portions to a mixture of (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-piperazine (0.5 g) and 1-methyl-1H-pyrazole-4-carboxaldehyde (0.12 g) in dichloromethane (10 ml) and the whole was stirred at room temperature for 1 hour. The mixture was washed with sodium hydrogen carbonate aqueous solution, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate as an eluent. The fractions containing the objective compound were collected and evaporated in vacuo to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-4-[(1-methyl-1H-pyrazol-4-yl)methyl]piperazine (0.54 g) as an oil.

Workup

  1. washThe mixture was washed with sodium hydrogen carbonate aqueous solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. additionThe fractions containing the objective compound
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d244733c373e4f7fab3ea480c9818262
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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