Formate → HCID 58727990, compound

HRID 1992071Notes

Reaction equation

HRID 1992071 reaction equation
C(O)(C(F)(F)F)=O.[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:18][N:17]=[C:16]([CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[N:15]=2)[CH2:10][CH2:9]1.[C:26]([N:34]1[CH2:39][CH2:38][C:37]([CH2:46][CH:47]=O)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:36][CH2:35]1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+].C([O-])=O>C(Cl)Cl>[C:26]([N:34]1[CH2:35][CH2:36][C:37]([CH2:46][CH2:47][N:8]2[CH2:9][CH2:10][CH:11]([C:14]3[O:18][N:17]=[C:16]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[N:15]=3)[CH2:12][CH2:13]2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:38][CH2:39]1)(=[O:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 6

HCID 283FormateHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 25132605HCID 25132605, compoundHCID 58961066HCID 58961066, compound

Product 1

HCID 58727990HCID 58727990, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The TFA salt of 3-[(5-piperidin-4-yl-1,2,4-oxadiazol-3-yl)methyl]pyridine (27 mg, 0.076 mmol) was combined with (1-benzoyl-4-phenylpiperidin-4-yl)acetaldehyde (21 mg, 0.069 mmol) in 2 mL DCM and treated with NaBH(OAc)3 (43 mg, 0.203 mmol) at ambient temperature with agitation for 18 h. 1 mL of saturated aqueous NaHCO3 was added and agitated 1 h. The organic phase was separated and concentrated. The crude product was purified by HPLC (METHOD) to give 3-[(5-{1-[2-(1-benzoyl-4-phenylpiperidin-4-yl)ethyl]piperidin-4-yl}-1,2,4-oxadiazol-3-yl)methyl]pyridine (14.2 mg, 0.024 mmol, 34%) as the formate salt. 1H NMR (300 MHz, CD3OD) δ 8.52-8.44 (m, 2H), 7.80 (d, 1H, J=7.9 Hz), 7.48-7.38 (m, 10H), 7.26 (m, 1H), 4.19 (m, 1H), 4.13 (s, 2H), 3.59 (m, 1H), 3.36-3.29 (m, 3H), 3.12-3.02 (m, 3H), 2.47-1.45 (m, 13H). ES-LCMS m/z 536.25 (M+H). HRMS C33H37N5O2 m/z 536.3026 (M+H)Cal. 536.3018 (M+H)Obs..

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated
  3. customThe crude product was purified by HPLC (METHOD)

Sources & evidence

ORD record
ord-c7b39b3327cc4bc1aa1e1880ea683987
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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