Dimethylamine → HCID 24800869, compound

HRID 386458Notes

Reaction equation

HRID 386458 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([C:19]3[O:20][C:21]([C:24]4[N:29]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:26][CH:25]=4)=[CH:22][N:23]=3)=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=O.[CH3:34][NH:35][CH3:36].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH3:34][N:35]([CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([C:19]3[O:20][C:21]([C:24]4[N:29]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:26][CH:25]=4)=[CH:22][N:23]=3)=[O:18])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1)[CH3:36]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86645815HCID 86645815, compound

Product 1

HCID 24800869HCID 24800869, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Methyl 6-(2-(3-(4′-formylbiphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate (19 mg, 0.043 mmol) and dimethylamine (2 M in THF, 0.026 mL, 0.052 mmol) were dissolved in dichloroethane (2 mL) and NaBH(OAc)3 (16 mg, 0.078 mmol) was added. The reaction solution was stirred under an atmosphere of Ar at ambient temperature for 2 h and then quenched with saturated aqueous NaHCO3. The crude product was extracted with EtOAc and the solvent was removed in vacuo. The crude product was purified with preparative thin layer chromatography (SiO2, 5% Et3N, 5% MeOH, 90% EtOAc) to furnish methyl 6-(2-(3-(4′-((dimethylamino)methyl)biphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate as a tan solid (5 mg, 25%): 1H NMR (CDCl3, 600 MHz) δ 8.12 (d, 1H, J=7.7 Hz), 8.03 (d, 2H, J=9.6 Hz), 7.97 (t, 1H, J=7.8 Hz), 7.53 (dd, 4H, J=8.0, 4.9 Hz), 7.38 (d, 2H, J=7.9 Hz), 7.34 (d, 2H, J=8.0 Hz), 4.03 (s, 3H), 3.51 (t, 4H, J=7.6 Hz), 3.15 (t, 2H, J=7.6 Hz), 2.31 (s, 6H); 13C NMR (CDCl3, 150 MHz) δ 187.3, 165.1, 157.4, 152.4, 148.5, 146.5, 139.4, 138.9, 138.3, 129.6, 128.9, 128.0, 127.2, 126.9, 125.2, 123.3, 63.8, 53.1, 45.1, 40.6, 29.3; HR ESI-TOF m/z 470.2071 (M+H+, C28H27N3O4, requires 470.2074).

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionThe crude product was extracted with EtOAc
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified with preparative thin layer chromatography (SiO2, 5% Et3N, 5% MeOH, 90% EtOAc)

Sources & evidence

ORD record
ord-63bd630bfccc4591897d9b217474f5b1
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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