Acetic Acid → HCID 11690827, compound

HRID 1170523Notes

Reaction equation

HRID 1170523 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([CH2:12][NH:13][C:14]([CH:16]3[CH2:20][CH2:19][CH2:18][NH:17]3)=[O:15])[CH:9]=[C:8]([CH3:21])[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O>[N:1]1([C:6]2[N:11]=[C:10]([CH2:12][NH:13][C:14]([CH:16]3[CH2:20][CH2:19][CH2:18][N:17]3[CH2:28][C:27]3[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:32])[F:33])=[CH:31][CH:30]=3)=[O:15])[CH:9]=[C:8]([CH3:21])[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679964-(Trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58654441HCID 58654441, compound

Product 1

HCID 11690827HCID 11690827, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of pyrrolidine-2-carboxylic acid (2-imidazol-1-yl-6-methyl-pyrimidin-4-ylmethyl)-amide (43 mg, 0.15 mmol) in dimethylformamide (1.5 mL) was added 4-(trifluoromethyl)benzaldehyde (22 μL, 0.16 mmol) and acetic acid (0.075 mL) at r.t. The solution was allowed to stir for 2 hrs. To the solution was added sodium triacetoxyborohydride (107 mg, 0.50 mmol) at r.t. The solution was stirred for 16 hrs then concentrated under vacuum. The residue was diluted with DCM, washed with NaOH (1N, 30 mL) and water (30 mL), dried over MgSO4, filtered and concentrated. The product was purified using mass-triggered LCMS to afford 5 mg of 1-(4-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid (2-imidazol-1-yl-6-methyl-pyrimidin-4-ylmethyl)-amide as a white solid. [M+H]+ 444.96.

Workup

  1. stirringThe solution was stirred for 16 hrs
  2. concentrationthen concentrated under vacuum
  3. additionThe residue was diluted with DCM
  4. washwashed with NaOH (1N, 30 mL) and water (30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified

Sources & evidence

ORD record
ord-8b3a22a836b14dbca891ab4b7872bc91
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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