Acetone → HCID 67092331, compound

HRID 2074087Notes

Reaction equation

HRID 2074087 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]3)=[O:14])[N:10]=[C:9]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:8]=2)=[CH:4][CH:3]=1.[CH3:30][C:31]([CH3:33])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([N:15]3[CH2:16][CH2:17][CH:18]([NH:21][CH:31]([CH3:33])[CH3:30])[CH2:19][CH2:20]3)=[O:14])[N:10]=[C:9]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)[CH:8]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 67092302HCID 67092302, compound

Product 1

HCID 67092331HCID 67092331, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine (0.3 g, 0.76 mmol) in CH2Cl2 (5 mL) was added acetone (56 μL, 0.76 mmol) and the solution was stirred for 15 minutes at room temperature. This was followed by the addition of NaBH(OAc)3 (0.242 g, 1.14 mmol) and the reaction mixture was stirred overnight at room temperature. The mixture was diluted with CH2Cl2 (20 mL) and 2 M NaOH and the bi-phasic solution was stirred for 20 minutes. The mixture was extracted with CH2Cl2 (2×25 mL) and the combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH) to give the title compound as a white solid (0.19 g, 44%). 1H NMR (400 MHz, DMSO-D6) δ ppm 8.51 (d, 2 H), 7.66 (d, 2 H), 7.30 (t, 2 H), 7.14 (t, 2 H), 6.51 (s, 1 H), 5.13-5.20 (m, 2 H), 4.07-4.16 (m, 1 H), 3.93 (s, 2 H), 3.77-3.87 (m, 1 H), 3.04-3.14 (m, 1 H), 2.83-2.93 (m, 1 H), 2.69-2.79 (m, 2 H), 1.72-1.86 (m, 5H); m/z (APCI+) for C25H30N5OF 436.1 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. stirringthe bi-phasic solution was stirred for 20 minutes
  3. extractionThe mixture was extracted with CH2Cl2 (2×25 mL)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-7c196bfd4c0343579b2d72ea5cb9ae06
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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